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Menthol
Menthol
is an organic compound made synthetically or obtained from corn mint, peppermint, or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (−)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol
Menthol
has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol
Menthol
also acts as a weak kappa opioid receptor agonist.

Contents

1 Structure 2 Biological properties 3 Occurrence 4 Biosynthesis 5 Production 6 Applications 7 Reactions 8 History 9 Compendial status 10 Safety 11 See also 12 References 13 Further reading 14 External links

Structure[edit] Natural menthol exists as one pure stereoisomer, nearly always the (1R,2S,5R) form (bottom left corner of the diagram below). The eight possible stereoisomers are:

In the natural compound, the isopropyl group is in the trans orientation to both the methyl and hydroxyl groups. Thus, it can be drawn in any of the ways shown:

The (+)- and (–)-enantiomers of menthol are the most stable among these based on their cyclohexane conformations. With the ring itself in a chair conformation, all three bulky groups can orient in equatorial positions. The two crystal forms for racemic menthol have melting points of 28 °C and 38 °C. Pure (−)-menthol has four crystal forms, of which the most stable is the α form, the familiar broad needles. Biological properties[edit]

A macro photograph of menthol crystals

Menthol
Menthol
crystals at room temperature. Approx. 1 cm in length.

Menthol's ability to chemically trigger the cold-sensitive TRPM8 receptors in the skin is responsible for the well-known cooling sensation it provokes when inhaled, eaten, or applied to the skin.[1] In this sense, it is similar to capsaicin, the chemical responsible for the spiciness of hot chilis (which stimulates heat sensors, also without causing an actual change in temperature). Menthol's analgesic properties are mediated through a selective activation of κ-opioid receptors.[2] Menthol
Menthol
also blocks voltage-sensitive sodium channels, reducing neural activity that may stimulate muscles.[3] A study showed that topical absorption of ibuprofen is not increased by menthol, but does note the complementary effect of the menthol as a pain reliever itself.[4] Some studies show that menthol acts as GABAA receptor
GABAA receptor
positive allosteric modulator and increases GABAergic transmission in PAG neurons.[5] Menthol
Menthol
also shares anaesthetic properties similar to propofol, by modulating the same sites of the GABAA receptor.[6] Menthol
Menthol
is widely used in dental care as a topical antibacterial agent, effective against several types of streptococci and lactobacilli.[7] Occurrence[edit] Mentha arvensis
Mentha arvensis
(wild mint) is the primary species of mint used to make natural menthol crystals and natural menthol flakes[citation needed]. This species is primarily grown in the Uttar Pradesh
Uttar Pradesh
region in India.[citation needed] Menthol
Menthol
occurs naturally in peppermint oil (along with a little menthone, the ester menthyl acetate and other compounds), obtained from Mentha
Mentha
× piperita (peppermint).[8] Japanese menthol also contains a small percentage of the 1-epimer, neomenthol.[citation needed] Biosynthesis[edit] The biosynthesis of menthol has been investigated in Mentha
Mentha
× piperita and the enzymes involved in have been identified and characterized.[9] It begins with the synthesis of the terpene limonene, followed by hydroxylation, and then several reduction and isomerization steps. More specifically, the biosynthesis of (−)-menthol takes place in the secretory gland cells of the peppermint plant. Geranyl diphosphate synthase (GPPS), first catalyzes the reaction of IPP and DMAPP into geranyl diphosphate. Next (−)-limonene synthase (LS) catalyzes the cyclization of geranyl diphosphate to (−)-limonene. (−)-Limonene-3-hydroxylase (L3OH), using O2 and NADPH, then catalyzes the allylic hydroxylation of (−)-limonene at the 3 position to (−)-trans-isopiperitenol. (−)-trans-Isopiperitenol dehydrogenase (iPD) further oxidizes the hydroxyl group on the 3 position using NAD+ to make (−)-isopiperitenone. (−)-Isopiperitenone reductase (iPR) then reduces the double bond between carbons 1 and 2 using NADPH
NADPH
to form (+)-cis-isopulegone. (+)-cis-Isopulegone isomerase (iPI) then isomerizes the remaining double bond to form (+)-pulegone. (+)- Pulegone
Pulegone
reductase (PR) then reduces this double bond using NADPH
NADPH
to form (−)-menthone. (−)- Menthone
Menthone
reductase (MR) then reduces the carbonyl group using NADPH
NADPH
to form (−)-menthol.[9]

Production[edit] Natural menthol is obtained by freezing peppermint oil. The resultant crystals of menthol are then separated by filtration. Total world production of menthol in 1998 was 12,000 tonnes of which 2,500 tonnes was synthetic. In 2005, the annual production of synthetic menthol was almost double. Prices are in the $10–20/kg range with peaks in the $40/kg region but have reached as high as $100/kg. In 1985, it was estimated that China produced most of the world's supply of natural menthol, although it appears that India
India
has pushed China into second place.[10] Menthol
Menthol
is manufactured as a single enantiomer (94% e.e.) on the scale of 3,000 tonnes per year by Takasago International Corporation.[11] The process involves an asymmetric synthesis developed by a team led by Ryōji Noyori, who won the 2001 Nobel Prize for Chemistry in recognition of his work on this process:

The process begins by forming an allylic amine from myrcene, which undergoes asymmetric isomerisation in the presence of a BINAP
BINAP
rhodium complex to give (after hydrolysis) enantiomerically pure R-citronellal. This is cyclised by a carbonyl-ene-reaction initiated by zinc bromide to isopulegol, which is then hydrogenated to give pure (1R,2S,5R)-menthol. Another commercial process is the Haarmann–Reimer process (after the company Haarmann & Reimer, now part of Symrise)[12] This process starts from m-cresol which is alkylated with propene to thymol. This compound is hydrogenated in the next step. Racemic
Racemic
menthol is isolated by fractional distillation. The enantiomers are separated by chiral resolution in reaction with methyl benzoate, selective crystallisation followed by hydrolysis.

Racemic
Racemic
menthol can also be formed by hydrogenation of pulegone. In both cases with further processing (crystallizative entrainment resolution of the menthyl benzoate conglomerate) it is possible to concentrate the L-enantiomer, however this tends to be less efficient, although the higher processing costs may be offset by lower raw material costs. A further advantage of this process is that D-menthol becomes inexpensively available for use as a chiral auxiliary, along with the more usual L-antipode.[13] Applications[edit] Menthol
Menthol
is included in many products for a variety of reasons. These include:

In nonprescription products for short-term relief of minor sore throat and minor mouth or throat irritation.

Examples: lip balms and cough medicines.

As an antipruritic to reduce itching. As a topical analgesic, it is used to relieve minor aches and pains, such as muscle cramps, sprains, headaches and similar conditions, alone or combined with chemicals such as camphor, eucalyptus oil or capsaicin. In Europe, it tends to appear as a gel or a cream, while in the U.S., patches and body sleeves are very frequently used.

Examples: Tiger Balm, or IcyHot
IcyHot
patches or knee/elbow sleeves.

As a penetration enhancer in transdermal drug delivery. In decongestants for chest and sinuses (cream, patch or nose inhaler).

Examples: Vicks VapoRub, Mentholatum, VapoRem.

In certain medications used to treat sunburns, as it provides a cooling sensation (then often associated with aloe). In aftershave products to relieve razor burn. As a smoking tobacco additive in some cigarette brands, for flavor, and to reduce throat and sinus irritation caused by smoking. Menthol also increases nicotine receptor density,[14] increasing the addictive potential of tobacco products.[15][16] Commonly used in oral hygiene products and bad-breath remedies, such as mouthwash, toothpaste, mouth and tongue sprays, and more generally as a food flavor agent; such as in chewing gum and candy. As a pesticide against tracheal mites of honey bees. In perfumery, menthol is used to prepare menthyl esters to emphasize floral notes (especially rose). In first aid products such as "mineral ice" to produce a cooling effect as a substitute for real ice in the absence of water or electricity (pouch, body patch/sleeve or cream). In various patches ranging from fever-reducing patches applied to children's foreheads to "foot patches" to relieve numerous ailments (the latter being much more frequent and elaborate in Asia, especially Japan: some varieties use "functional protrusions", or small bumps to massage one's feet as well as soothing them and cooling them down). In some beauty products such as hair conditioners, based on natural ingredients (e.g., St. Ives). As an antispasmodic and smooth muscle relaxant in upper gastrointestinal endoscopy.[17]

In organic chemistry, menthol is used as a chiral auxiliary in asymmetric synthesis. For example, sulfinate esters made from sulfinyl chlorides and menthol can be used to make enantiomerically pure sulfoxides by reaction with organolithium reagents or Grignard reagents. Menthol
Menthol
reacts with chiral carboxylic acids to give diastereomic menthyl esters, which are useful for chiral resolution. Reactions[edit] Menthol
Menthol
reacts in many ways like a normal secondary alcohol. It is oxidised to menthone by oxidising agents such as chromic acid or dichromate,[18] though under some conditions the oxidation can go further and break open the ring. Menthol
Menthol
is easily dehydrated to give mainly 3-menthene, by the action of 2% sulfuric acid. Phosphorus pentachloride (PCl5) gives menthyl chloride.

History[edit] In the West, menthol was first isolated in 1771, by Hieronymus David Gaubius.[19] Early characterizations were done by Oppenheim,[20] Beckett,[21] Moriya,[22] and Atkinson.[23] It was named by F. L. Alphons Oppenheim (1833–1877) in 1861.[24] Compendial status[edit]

United States Pharmacopeia 23[25][clarification needed] Japanese Pharmacopoeia 15[26] Food Chemicals Codex[27]

Safety[edit] The estimated lethal dose for menthol (and peppermint oil) in humans may be as low as 2 g. Survival after doses of 8 to 9 g have been reported.[28] Overdose effects are abdominal pain, ataxia, atrial fibrillation, bradycardia, coma, dizziness, lethargy, nausea, skin rash, tremor, vomiting, vertigo.[29] See also[edit]

Aroma compound Carvone Chlorobutanol Ethyl benzoate Ethyl salicylate Menthoxypropanediol Methyl
Methyl
salicylate Menthol
Menthol
cigarettes Menthyl isovalerate p-Menthane-3,8-diol Thujone Vapor pressure

References[edit]

^ Eccles, R. (1994). " Menthol
Menthol
and Related Cooling Compounds". J. Pharm. Pharmacol. 46 (8): 618–630. doi:10.1111/j.2042-7158.1994.tb03871.x. PMID 7529306.  ^ Galeotti, N.; Mannelli, L. D. C.; Mazzanti, G.; Bartolini, A.; Ghelardini, C.; Di Cesare, Mannelli (2002). "Menthol: a natural analgesic compound". Neurosci. Lett. 322 (3): 145–148. doi:10.1016/S0304-3940(01)02527-7. PMID 11897159.  ^ Haeseler, G.; Maue, D.; Grosskreutz, J.; Bufler, J.; Nentwig, B.; Piepenbrock, S.; Dengler, R.; Leuwer, M. (2002). "Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol". Eur. J. Anaesthes. 19 (8): 571–579. doi:10.1017/S0265021502000923.  ^ Brain, K. R.; Green, D. M.; Dykes, P. J.; Marks, R.; Bola, T. S. (2006). "The role of menthol in skin penetration from topical formulations of ibuprofen 5% in vivo". Skin Pharmacol. Physiol. 19 (1): 17–21. doi:10.1159/000089139. PMID 16247245.  ^ Lau, Benjamin K.; Karim, Shafinaz; Goodchild, Ann K.; Vaughan, Christopher W.; Drew, Geoffrey M. (2014-06-01). " Menthol
Menthol
enhances phasic and tonic GABAA receptor-mediated currents in midbrain periaqueductal grey neurons". Br. J. Pharmacol. 171 (11): 2803–2813. doi:10.1111/bph.12602. ISSN 1476-5381. PMC 4243856 . PMID 24460753.  ^ Watt, Erin E.; Betts, Brooke A.; Kotey, Francesca O.; Humbert, Danielle J.; Griffith, Theanne N.; Kelly, Elizabeth W.; Veneskey, Kelley C.; Gill, Nikhila; Rowan, Kathleen C. (2008-08-20). "Menthol shares general anesthetic activity and sites of action on the GABAA receptor with the intravenous agent, propofol". Eur. J. Pharmacol. 590 (1–3): 120–126. doi:10.1016/j.ejphar.2008.06.003. ISSN 0014-2999. PMID 18593637.  ^ Freires, I. A.; Denny, C.; Benso, B.; de Alencar, S. M.; Rosalen, P. L. (2015-04-22). "Antibacterial Activity of Essential Oils and Their Isolated Constituents against Cariogenic Bacteria: A Systematic Review". Molecules. 20 (4): 7329–7358. doi:10.3390/molecules20047329. PMID 25911964.  ^ PDR for Herbal Medicines (4th ed.). Thomson Healthcare. p. 640. ISBN 978-1-56363-678-3.  ^ a b Croteau, R. B.; Davis, E. M.; Ringer, K. L.; Wildung, M. R. (December 2005). "(−)- Menthol
Menthol
biosynthesis and molecular genetics". Naturwissenschaften. 92 (12): 562–577. Bibcode:2005NW.....92..562C. doi:10.1007/s00114-005-0055-0. PMID 16292524.  ^ Charles S. Sell (2013), "Terpenoids", in Arza Seidel; et al., Kirk-Othmer Chemical Technology of Cosmetics, pp. 247–374, ISBN 978-1-118-40692-2 CS1 maint: Explicit use of et al. (link) ^ "Japan: Takasago to Expand L- Menthol
Menthol
Production in Iwata Plant". Flex News Food.  ^ Schäfer, Bernd (2013). "Menthol". Chemie in unserer Zeit. 47 (3): 174–182. doi:10.1002/ciuz.201300599.  ^ Sell, Charles (ed.). The Chemistry of Fragrances: From Perfumer to Consumer. ISBN 978-085404-824-3. [page needed] ^ Henderson, B. J.; Wall, T. R.; Henley, B. M.; Kim, C. H.; Nichols, W. A.; Moaddel, R.; Xiao, C.; Lester, H. A. (2016). " Menthol
Menthol
Alone Upregulates Midbrain nAChRs, Alters nAChR Subtype Stoichiometry, Alters Dopamine Neuron Firing Frequency, and Prevents Nicotine Reward". J. Neurosci. 36 (10): 2957–2974. doi:10.1523/JNEUROSCI.4194-15.2016. PMC 4783498 . PMID 26961950.  ^ Biswas, L.; Harrison, E.; Gong, Y.; Avusula, R.; Lee, J.; Zhang, M.; Rousselle, T.; Lage, J.; Liu, X. (2016). "Enhancing effect of menthol on nicotine self-administration in rats". Psychopharmacology. 233: 3417–3427. doi:10.1007/s00213-016-4391-x. PMID 27473365.  ^ Wickham, R. J. (2015). "How Menthol
Menthol
Alters Tobacco-Smoking Behavior: A Biological Perspective". Yale J. Biol. Med. 88 (3): 279–287. PMC 4553648 . PMID 26339211.  ^ Hiki, N.; Kaminishi, M.; Hasunuma, T.; Nakamura, M.; Nomura, S.; Yahagi, N.; Tajiri, H.; Suzuki, H. (2011). "A Phase I Study Evaluating Tolerability, Pharmacokinetics, and Preliminary Efficacy of L-Menthol in Upper Gastrointestinal Endoscopy". Clin. Pharmacol. Therapeu. 90 (2): 221–228. doi:10.1038/clpt.2011.110.  ^ Sandborn, L. T. "l-Menthone". Organic Syntheses. ; Collective Volume, 1, p. 340  ^ Adversoriorum varii argumentii. 1. Leiden. 1771. p. 99.  ^ Oppenheim, A. (1862). "On the camphor of peppermint". J. Chem. Soc. 15: 24. doi:10.1039/JS8621500024.  ^ Beckett, G. H.; Alder Wright, C. R. (1876). "Isomeric terpenes and their derivatives (Part V)". J. Chem. Soc. 29: 1. doi:10.1039/JS8762900001.  ^ Moriya, M. (1881). "Contributions from the Laboratory of the University of Tôkiô, Japan. No. IV. On menthol or peppermint camphor". J. Chem. Soc., Trans. 39: 77. doi:10.1039/CT8813900077.  ^ Atkinson, R. W.; Yoshida, H. (1882). "On peppermint camphor (menthol) and some of its derivatives". J. Chem. Soc., Trans. 41: 49. doi:10.1039/CT8824100049.  ^ Oppenheim, A. (1861). "Note sur le camphre de menthe" [On the camphor of mint]. Comptes rendus. 53: 379–380. Les analogies avec le bornéol me permettent de proposer pour ce corps le nom de menthol,… [Analogies with borneol allow me to propose the name menthol for this substance,…]  ^ Therapeutic Goods Administration (1999). "Approved Terminology for Medicines" (PDF). Retrieved 2009-06-29.  ^ "Japanese Pharmacopoeia". Retrieved 2009-06-29.  ^ Sigma Aldrich. "DL-Menthol". Retrieved 2009-06-29.  ^ James A. Duke (2002), "PEPPERMINT", Handbook of Medicinal Herbs (2nd ed.), pp. 562–564, ISBN 0-8493-1284-1  ^ Jerrold B. Leikin; Frank P. Paloucek, eds. (2008), " Peppermint
Peppermint
Oil", Poisoning and Toxicology Handbook (4th ed.), Informa, p. 885, ISBN 978-1-4200-4479-9 

Further reading[edit]

Turner, E. E.; Harris, M. M. (1952). Organic Chemistry. London: Longmans, Green & Co.  Handbook of Chemistry and Physics (71st ed.). Ann Arbor, MI: CRC Press. 1990.  The Merck Index (7th ed.). Rahway, NJ: Merck & Co. 1960.  Perfumer & Flavorist. 32 (12): 38–47. 2007.  Missing or empty title= (help)

External links[edit]

Wikimedia Commons has media related to Menthol.

Colacot, T. J. (2002-04-01). "2001 Nobel Prize in Chemistry: Timely recognition for rhodium, ruthenium and osmium-catalysed chiral reactions". Platinum Metals Rev. 46 (2): 82–83.  Ryoji Noyori Nobel lecture (2001) Menthol
Menthol
Information A review of menthol from the Science Creative Quarterly

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positive modulators

Alcohols

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(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital

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Lirequinil
(Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684

Phenols

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Quinazolinones

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Volatiles/gases

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betaine Chloral
Chloral
hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether

Others/unsorted

3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate
Menthyl isovalerate
(validolum) Monastrol Niacin Nicotinamide
Nicotinamide
(niacinamide) Org 25,435 Phenytoin Propanidid Retigabine
Retigabine
(ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)

Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

v t e

Opioid
Opioid
receptor modulators

MOR

Agonists (abridged; see here for a full list): 3-HO-PCP 7-Acetoxymitragynine 7-Hydroxymitragynine ψ-Akuammigine α-Chlornaltrexamine α-Narcotine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin
Adrenorphin
(metorphamide) AH-7921 Akuammicine Akuammidine Alfentanil Anileridine Apparicine β-Endorphin BAM-12P BAM-18P BAM-22P Benzhydrocodone Benzylmorphine Bezitramide Biphalin BU08070 Buprenorphine Butorphan Butorphanol Butyrfentanyl BW-373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO
DAMGO
(DAGO) Dermorphin Desmetramadol
Desmetramadol
(desmethyltramadol) Desomorphine Dextromoramide Dextropropoxyphene
Dextropropoxyphene
(propoxyphene) Dezocine Dimenoxadol Dimethylaminopivalophenone Eluxadoline Diamorphine (heroin) Dihydrocodeine Dihydroetorphine Dihydromorphine Diphenoxylate Dipipanone Dynorphin A Embutramide Endomorphin-1 Endomorphin-2 Eseroline Ethylmorphine Etorphine Fentanyl Fluorophen Frakefamide Furanylfentanyl Hemorphin-4 Herkinorin Hodgkinsine Hydrocodone Hydromorphinol Hydromorphone IBNtxA Ketamine Ketobemidone Kratom Laudanosine Lefetamine Leu-enkephalin Levacetylmethadol Levomethorphan Levorphanol Lexanopadol Loperamide Loxicodegol Matrine Meptazinol Met-enkephalin
Met-enkephalin
(metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine
Mitragynine
pseudoindoxyl Morphiceptin Morphine Nalbuphine Nalbuphine
Nalbuphine
sebacate NalBzOH Nalmexone Naltalimide Neopine NFEPP Nicocodeine Nicodicodeine Nicomorphine NKTR-181 Norketamine Octreotide Oliceridine OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphonazine Oxymorphone Oxymorphone
Oxymorphone
phenylhydrazone OxyPNPH Papaver somniferum
Papaver somniferum
(opium) Pentazocine Pericine Pethidine
Pethidine
(meperidine) Phenazocine Phencyclidine Piminodine Piritramide PL-017 Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 Tubotaiwine U-47700 Valorphin Viminol Xorphanol

PAMs: BMS-986121 BMS-986122

Antagonists: (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 3CS-nalmefene 4-Caffeoyl-1,5-quinide 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC α-Gliadin β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin
Catechin
gallate Clocinnamox CTAP CTOP Cyclofoxy Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Ginsenoside R Hyperoside Ibogaine Levallorphan Lobeline LY-255582 LY-2196044 Methocinnamox Methylnaltrexone Methylsamidorphan chloride Naldemedine Nalmefene Nalodeine
Nalodeine
(N-allylnorcodeine) Nalorphine Nalorphine
Nalorphine
dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexazone Naltrexonazine Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin

Unknown/unsorted: Cannabidiol Coronaridine Cyproterone acetate Dihydroakuuamine Tabernanthine Tetrahydrocannabinol

DOR

Agonists: 3CS-nalmefene 6'-GNTI 7-SIOM ADL-5747 (PF-04856881) ADL-5859 Alazocine
Alazocine
(SKF-10047) Amoxapine AR-M100390 (ARM390) AZD2327 β-Endorphin BAM-18P Biphalin BU-48 Butorphan Butorphanol BW-373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin
Deltorphin
A Deltorphin
Deltorphin
I Deltorphin
Deltorphin
II Desmethylclozapine Desmetramadol
Desmetramadol
(desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 DSLET Ethylketazocine Etorphine Fentanyl FIT Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone JNJ-20788560 KNT-127 Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lexanopadol Lofentanil Met-enkephalin
Met-enkephalin
(metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine
Mitragynine
pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine NalBzOH Oripavine Oxycodone Oxymorphone Pethidine
Pethidine
(meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SB-235863 SNC-80 SNC-162 TAN-67
TAN-67
(SB-205,607) TH-030418 Thebaine Thiobromadol
Thiobromadol
(C-8813) Tonazocine Tramadol TRV250 Xorphanol Zenazocine

Antagonists: 4',7-Dihydroxyflavone 5'-NTII 6β-Naltrexol 6β-Naltrexol-d4 α-Santolol β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran BNTX Catechin Catechin
Catechin
gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin ICI-154129 ICI-174864 LY-255582 LY-2196044 Methylnaltrexone Methylnaltrindole N-Benzylnaltrindole Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SDM25N SoRI-9409 Taxifolin Thienorphine

Unknown/unsorted: 18-MC Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol

KOR

Agonists: 3CS-nalmefene 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin
Adrenorphin
(metorphamide) Akuuamicine Alazocine
Alazocine
(SKF-10047) Allomatrine Apadoline Asimadoline BAM-12P BAM-18P BAM-22P Big dynorphin Bremazocine BRL-52537 Butorphan Butorphanol BW-373U86 Cebranopadol Ciprefadol CR665 Cyclazocine Cyclorphan Cyprenorphine Desmetramadol
Desmetramadol
(desmethyltramadol) Diamorphine (heroin) Diacetylnalorphine Difelikefalin Dihydroetorphine Dihydromorphine Diprenorphine Dynorphin A Dynorphin B
Dynorphin B
(rimorphin) Eluxadoline Enadoline Eptazocine Erinacine E Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 GR-103545 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lexanopadol Lofentanil LPK-26 Lufuradom Matrine MB-1C-OH Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine Nalbuphine
Nalbuphine
sebacate NalBzOH Nalfurafine Nalmefene Nalodeine
Nalodeine
(N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxilorphan Oxycodone Pentazocine Pethidine
Pethidine
(meperidine) Phenazocine Proxorphan Racemethorphan Racemorphan RB-64 Salvinorin A
Salvinorin A
(salvia) Salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether Samidorphan Spiradoline
Spiradoline
(U-62,066) TH-030418 Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50,488 U-54,494A U-69,593 Xorphanol

Antagonists: 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone ANTI Apigenin Arodyne AT-076 Axelopran AZ-MTAB Binaltorphimine BU09059 Buprenorphine Catechin Catechin
Catechin
gallate CERC-501
CERC-501
(LY-2456302) Clocinnamox Cyclofoxy Dezocine DIPPA EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2196044 LY-2444296 LY-2459989 LY-2795050 MeJDTic Methylnaltrexone ML190 ML350 MR-2266 N-Fluoropropyl-JDTic Naloxone Naltrexone Naltrindole Naringenin Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin UPHIT Zyklophin

Unknown/unsorted: Akuammicine Akuammine Coronaridine Cyproterone acetate Dihydroakuuamine Ibogamine Tabernanthine

NOP

Agonists: (Arg14,Lys15)Nociceptin ((pF)Phe4)Nociceptin(1-13)NH2 (Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2 Ac-RYYRWK-NH2 Ac-RYYRIK-NH2 BU08070 Buprenorphine Cebranopadol Dihydroetorphine Etorphine JNJ-19385899 Levomethorphan Levorphanol Levorphanol Lexanopadol MCOPPB MT-7716 NNC 63-0532 Nociceptin
Nociceptin
(orphanin FQ) Nociceptin
Nociceptin
(1-11) Nociceptin
Nociceptin
(1-13)NH2 Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 Ro65-6570 SCH-221510 SCH-486757 SR-8993 SR-16435 TH-030418

Antagonists: (Nphe1)Nociceptin(1-13)NH2 AT-076 BAN-ORL-24 BTRX-246040
BTRX-246040
(LY-2940094) J-113397 JTC-801 NalBzOH Nociceptin
Nociceptin
(1-7) Nocistatin SB-612111 SR-16430 Thienorphine Trap-101 UFP-101

Unsorted

β-Casomorphins Amidorphin BAM-20P Cytochrophin-4 Deprolorphin Gliadorphin
Gliadorphin
(gluteomorphin) Gluten exorphins Hemorphins Kava
Kava
constituents MEAGL MEAP NEM Neoendorphins Nepetalactone
Nepetalactone
(catnip) Peptide B Peptide E Peptide F Peptide I Rubiscolins Soymorphins

Others

Enkephalinase inhibitors: Amastatin BL-2401 Candoxatril D -Phenylalanine Dexecadotril (retorphan) Ecadotril
Ecadotril
(sinorphan) Kelatorphan Racecadotril
Racecadotril
(acetorphan) RB-101 RB-120 RB-3007 Opiorphan Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex
Ubenimex
(bestatin)

Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Pronociceptin Proopiomelanocortin
Proopiomelanocortin
(POMC)

Others: Kyotorphin
Kyotorphin
(met-enkephalin releaser/degradation stabilizer)

See also: Receptor/signaling modulators • Signaling peptide/protein receptor modulators

v t e

TRP channel modulators

TRPA

Activators

4-Hydroxynonenal 4-Oxo-2-nonenal 4,5-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandin J2 α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Acrolein Allicin
Allicin
(garlic) Allyl isothiocyanate
Allyl isothiocyanate
(mustard, radish, horseradish, wasabi) AM404 Bradykinin Cannabichromene
Cannabichromene
(cannabis) Cannabidiol
Cannabidiol
(cannabis) Cannabigerol
Cannabigerol
(cannabis) Cinnamaldehyde
Cinnamaldehyde
(cinnamon) CR gas
CR gas
(dibenzoxazepine; DBO) CS gas
CS gas
(2-chlorobenzal malononitrile) Curcumin
Curcumin
(turmeric) Dehydroligustilide (celery) Diallyl disulfide Dicentrine
Dicentrine
( Lindera
Lindera
spp.) Farnesyl thiosalicylic acid Formalin Gingerols (ginger) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate Ligustilide (celery, Angelica acutiloba) Linalool
Linalool
(Sichuan pepper, thyme) Methylglyoxal Methyl
Methyl
salicylate (wintergreen) N-Methylmaleimide Nicotine
Nicotine
(tobacco) Oleocanthal
Oleocanthal
(olive oil) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) PF-4840154 Phenacyl chloride Polygodial
Polygodial
(Dorrigo pepper) Shogaols (ginger, Sichuan and melegueta peppers) Tear gases Tetrahydrocannabinol
Tetrahydrocannabinol
(cannabis) Thiopropanal S-oxide
Thiopropanal S-oxide
(onion) Umbellulone
Umbellulone
(Umbellularia californica) WIN 55,212-2

Blockers

Dehydroligustilide (celery) Nicotine
Nicotine
(tobacco) Ruthenium red

TRPC

Activators

Adhyperforin
Adhyperforin
(St John's wort) Diacyl glycerol GSK1702934A Hyperforin
Hyperforin
(St John's wort) Substance P

Blockers

DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators

ADP-ribose BCTC Calcium
Calcium
(intracellular) Cold Coolact P Cooling Agent 10 CPS-369 Eucalyptol
Eucalyptol
(eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol
Menthol
(mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g., stevioside) (Stevia rebaudiana) Sweet tastants (e.g., glucose, fructose, sucrose; indirectly) Thio-BCTC WS-3 WS-12 WS-23

Blockers

Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-amylcinnamoyl)anthranilic acid Nicotine
Nicotine
(tobacco) Niflumic acid Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO

TRPML

Activators

MK6-83 PI(3,5)P2 SF-22

TRPP

Activators

Triptolide
Triptolide
(Tripterygium wilfordii)

Blockers

Ruthenium red

TRPV

Activators

2-APB 5',6'-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Allicin
Allicin
(garlic) AM404 Anandamide Bisandrographolide (Andrographis paniculata) Camphor
Camphor
(camphor laurel, rosemary, camphorweed, African blue basil, camphor basil) Cannabidiol
Cannabidiol
(cannabis) Cannabidivarin
Cannabidivarin
(cannabis) Capsaicin
Capsaicin
(chili pepper) Carvacrol
Carvacrol
(oregano, thyme, pepperwort, wild bergamot, others) DHEA Diacyl glycerol Dihydrocapsaicin
Dihydrocapsaicin
(chili pepper) Estradiol Eugenol
Eugenol
(basil, clove) Evodiamine
Evodiamine
(Euodia ruticarpa) Gingerols (ginger) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin
Homocapsaicin
(chili pepper) Homodihydrocapsaicin
Homodihydrocapsaicin
(chili pepper) Incensole
Incensole
(incense) Lysophosphatidic acid Low pH (acidic conditions) Menthol
Menthol
(mint) N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide
Nonivamide
(PAVA) (PAVA spray) Nordihydrocapsaicin
Nordihydrocapsaicin
(chili pepper) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) Phorbol esters
Phorbol esters
(e.g., 4α-PDD) Piperine
Piperine
(black pepper, long pepper) Polygodial
Polygodial
(Dorrigo pepper) Probenecid Protons RhTx Rutamarin (Ruta graveolens) Resiniferatoxin
Resiniferatoxin
(RTX) (Euphorbia resinifera/pooissonii) Shogaols (ginger, Sichuan and melegueta peppers) Tetrahydrocannabivarin
Tetrahydrocannabivarin
(cannabis) Thymol
Thymol
(thyme, oregano) Tinyatoxin
Tinyatoxin
(Euphorbia resinifera/pooissonii) Tramadol Vanillin
Vanillin
(vanilla) Zucapsaicin

Blockers

α- Spinasterol
Spinasterol
( Vernonia
Vernonia
tweediana) AMG-517 Asivatrep BCTC Cannabigerol
Cannabigerol
(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol
Cannabinol
(cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047 Lanthanum Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid NGD-8243 Niflumic acid Pregnenolone sulfate RN-1734 RN-9893 Ruthenium red SB-705498 Tivanisiran Tolfenamic acid

See also: Receptor/signaling modulators • Ion channel modulators

v t e

Types of Terpenes and Terpenoids (# of isoprene units)

Basic forms:

Acyclic (linear, cis and trans forms) Monocyclic (single ring) Bicyclic (2 rings) Iridoids (cyclopentane ring) Iridoid
Iridoid
glycosides (iridoids bound to a sugar) Steroids (4 rings)

Hemiterpenoids (1)

Isoprene
Isoprene
(C5H8) Prenol Isovaleric acid

Monoterpene
Monoterpene
(C10H16)(2)

Acyclic

Ocimene Myrcenes

Monocyclic

Limonene Terpinene Phellandrene Umbellulone

Bicyclic

Pinene
Pinene
(β and α Camphene Thujene Sabinene Carene

Monoterpenoids (2,modified)

Acyclic

Linalool Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate

Monocyclic

Grapefruit mercaptan menthol p-Cymene thymol Perillyl alcohol Carvacrol

Bicyclic

Camphor Borneol Eucalyptol Halomon Eucalyptol Pinene Ascaridole

Sesquiterpenoids
Sesquiterpenoids
(3)

Farnesyl pyrophosphate Artemisinin Bisabolol

Diterpenoids (4)

Geranylgeranyl pyrophosphate Gibberellin Retinol Retinal Phytol Taxol Forskolin Aphidicolin Salvinorin A

Sesterterpenoids (5)

geranylfarnesol

Triterpenoids (6)

Steroids

Phytosterols

Campesterol beta Sitosterol gamma sitosterol Stigmasterol

Tocopherols Cholesterol Testosterone Cholecalciferol
Cholecalciferol
(Vit D) Ecdysones

Other

Saponins Squalane Lanosterol Acids

Oleanolic acid Ursolic acid Betulinic acid Moronic acid

Sesquarterpenes/oids (7)

ferrugicadiol tetraprenylcurcumene

Tetraterpenoids (Carotenoids) (8)

Carotenes

Alpha-Carotene Beta-Carotene Gamma-Carotene Delta-Carotene Lycopene Neurosporene Phytofluene Phytoene

Xanthophylls:

Canthaxanthin Cryptoxanthin Zeaxanthin Astaxanthin Lutein Rubixanthin

Polyterpenoids (many)

sap, resins, latex of many plants, e.g. rubber

Norisoprenoids (modified)

3-oxo-α-ionol 7,8-dihydroionone

Synthesis

Terpene
Terpene
synthase enzymes (many), having in common a Terpene
Terpene
synthase N terminal domain (protein domain)

Activated isoprene forms

Isopentenyl pyrophosphate
Isopentenyl pyrophosphate
(IPP) Dimethylallyl pyrophosphate
Dimethylallyl pyrophosphate
(DMAPP)

Authority control

LCCN: sh85083726 GND: 4378972-9 BNF: cb1374

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