Lysergic acid hydroxyethylamide (LSH or LAH), also known as lysergic acid ''N''-(α-hydroxyethyl)amide, is an ergoamide and an

ergoline Ergoline is a core structure in many alkaloids and their synthetic derivatives. Ergoline alkaloids were first characterized in ergot. Some of these are implicated in the condition of ergotism, which can take a convulsive form or a gangrenous for ...

. It is perhaps the main constituent of the parasitic

fungus A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...

, ''

Claviceps paspali ''Claviceps paspali'' is a fungus of the genus ''Claviceps'' (ergot) and family ''Clavicipitaceae''. Along with the better-known ''Claviceps purpurea'', it is one of the ''Claviceps'' species that has the capacity to produce psychedelic lysergami ...

''; and found in trace amounts in ''

Claviceps purpurea ''Claviceps purpurea'' is an ergot fungus that grows on the ear (botany), ears of rye and related cereal and forage plants. Consumption of Cereal, grains or seeds contaminated with the survival structure of this fungus, the ergot sclerotium, can ...

''. ''C. paspali'' and ''C. purpurea'' are ergot-spreading fungi. ''Periglandula'', ''Clavicipitacepus'' fungi, are permanently symbiotically connected to an estimated 450species of ''

Convolvulaceae Convolvulaceae (), commonly called the bindweed, bindweeds or morning glory, morning glories, is a Family (biology), family of about 60 genera and more than 1,650 species. These species are primarily herbaceous vines, but also include trees, sh ...

'' and thus generate LAH in some of them (42 generate ergolines, by Eckart Eich's review). The most well-known ones are ''

Ipomoea tricolor ''Ipomoea tricolor'', the Mexican morning glory or just morning glory, is a species of flowering plant in the family (biology), family Convolvulaceae, native plant, native to the tropics of the Americas, and widely cultivated and naturalisation ...

'' (“morning glory”), ''

Turbina corymbosa ''Ipomoea corymbosa'' (''Rivea corymbosa'', ''Turbina corymbosa'') is a species of morning glory, native throughout Latin America from Mexico as far south as Peru and widely naturalised elsewhere. Its common names include Christmasvine, Christmas ...

'' (''coaxihuitl''), and ''

Argyreia nervosa ''Argyreia nervosa'' is a perennial climbing vine native to the Indian subcontinent and introduced to numerous areas worldwide, including Hawaii, Africa, and the Caribbean. Though it can be invasive, it is often prized for its aesthetic and med ...

'' (Hawaiian baby woodrose). LAH is structurally similar to

ergonovine Ergonovine, also known as ergometrine and lysergic acid propanolamide, is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth. It can be used either by mouth, by injection into a muscle, or i ...

, which is also known as lysergic acid hydroxymethylethylamide. The more well-known analog, lysergic acid amide (syn. ''ergine''), is more prominent in analytical results because LAH easily decomposes to ergine. Ergine is only present because of the decomposition of LAH (and lysergic acid hydroxymethylethylamide and ergopeptines or their ergopeptam precursors); it is not generated. Indeed, a 2016 analysis found that fresher I. tricolor seeds contained more LAH than the other two batches analyzed ( another interesting finding is that penniclavine was the predominant ergoline.)

Pharmacology

The

pharmacology Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur betwee ...

of LSH has been very limitedly studied. It has about 30 to 50% of the

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...

ergometrine Ergonovine, also known as ergometrine and lysergic acid propanolamide, is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth. It can be used either by mouth, by injection into a muscle, or ...

as an

oxytocic A uterotonic, also known as an oxytocic or ecbolic, is a type of medication used to induce contraction or greater tonicity of the uterus. Uterotonics are used both to induce labor and to reduce postpartum hemorrhage. Labor induction in the thi ...

in the isolated guinea pig and rabbit

uterus The uterus (from Latin ''uterus'', : uteri or uteruses) or womb () is the hollow organ, organ in the reproductive system of most female mammals, including humans, that accommodates the embryonic development, embryonic and prenatal development, f ...

, produces sympathomimetic effects (including

piloerection Goose bumps, goosebumps or goose pimples are the bumps on a person's skin at the base of body hairs which may involuntarily develop when a person is tickled, cold or experiencing strong emotions such as fear, euphoria or sexual arousal. The f ...

mydriasis Mydriasis is the Pupillary dilation, dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, Physical trauma, trauma, or the use of c ...

, and

hyperthermia Hyperthermia, also known as overheating, is a condition in which an individual's body temperature is elevated beyond normal due to failed thermoregulation. The person's body produces or absorbs more heat than it dissipates. When extreme te ...

) very similar to those of

ergine Ergine, also known as lysergic acid amide (LSA or LAA) as well as LA-111, is a psychoactive compound of the ergoline and lysergamide families related to lysergic acid diethylamide (LSD). Ergine is an ergoline alkaloid found in fungi such as ...

in mice and rabbits, and has weak

ergotamine Ergotamine, sold under the brand name Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It is structurally similar to several neurotransmitter ...

-like

sympatholytic A sympatholytic (sympathoplegic) drug is a medication that opposes the downstream effects of postganglionic nerve firing in effector organs innervated by the sympathetic nervous system (SNS). They are indicated for various functions; for example, t ...

antiadrenergic An adrenergic antagonist is a drug that inhibits the function of adrenergic receptors. There are five adrenergic receptors, which are divided into two groups. The first group of receptors are the beta (β) adrenergic receptors. There are Beta-1 ad ...

effects (1/200 the potency of ergotamine). These effects are potentially indicative of LSH having LSD-like activity. However, LSH is not known to have been tested in humans. LSH may simply function as a

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

of ergine.

Chemistry

The

structure A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as ...

of LSH is similar to that of

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

, with the ''N'',''N''-diethylamide group replaced by an ''N''-(1-hydroxyethyl)amide in -lysergic acid α-hydroxyethylamide. LSH is also very similar in structure to

(ergometrine), which is also known as lysergic acid hydroxyisopropylamide.

Legal status

ᴅ-lysergic acid α-hydroxyethylamide is unscheduled and uncontrolled in the United States, but possession and sales of it for human consumption could potentially be prosecuted under the

Federal Analog Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

because of its structural similarities to

. Although doubtful as it breaks down into LSA which is a Schedule 3 drug and therefore not applicable to the

References

External links

Ergot - A Rich Source of Pharmacologically Active Substances
by Albert Hofmann {{Ergolines 5-HT2A agonists Ergot alkaloids Psychedelic lysergamides Secondary alcohols

Pharmacology

Chemistry

Legal status

See also

References

External links