Hodgkinsine is an
alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
found in plants of the genus ''
Psychotria
''Psychotria'' is a genus of flowering plants in the Family (biology), family Rubiaceae. It contains 1,582 species and is therefore one of the largest genera of flowering plants. The genus has a pantropical distribution and members of the genus a ...
'', particularly ''
Psychotria colorata'', although it is also found in ''
Psychotria lyciiflora
''Psychotria'' is a genus of flowering plants in the family Rubiaceae. It contains 1,582 species and is therefore one of the largest genera of flowering plants. The genus has a pantropical distribution and members of the genus are small understor ...
'' and probably other species in this family,
Hodgkinsine has
antiviral, antibacterial and antifungal effects, but has mainly been researched for the
analgesic effects that it produces, and is thought to be one of the components responsible for the analgesic effects seen when ''Psychotria colorata'' is used in traditional medical practice in humans. It has been found to act as both a
mu opioid agonist and an
NMDA antagonist
NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the ''N''-Methyl-D-aspartate receptor ( NMDAR). They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce ...
, both of which are mechanisms of action shared with commonly used painkillers (
morphine
Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. T ...
and
ketamine
Ketamine is a dissociative anesthetic used medically for induction and maintenance of anesthesia. It is also used as a recreational drug. It is one of the safest anesthetics, as, in contrast with opiates, ether, and propofol, it suppresses ...
respectively, and which occur concurrently in the clinical analgesics
tramadol
Tramadol, sold under the brand name Ultram among others, is an opioid pain medication used to treat moderate to moderately severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an ...
and
levorphanol
Levorphanol (brand name Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan.
It was first described in Ge ...
).
Hodgkinsine is a
trimer composed of three pyrrolidinoindoline subunits, with the
monomer
In chemistry, a monomer ( ; '' mono-'', "one" + ''-mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization.
Classification
...
closely resembling another alkaloid
eseroline
Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it ...
which has similar bioactivity. Due to its complex structure and multiple chiral centres, hodgkinsine has many
stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
s and significant research has been undertaken to elucidate the structure-activity relationships of the various isomers and synthetic derivatives structurally derived from hodgkinsine.
See also
*
Psychotridine
References
{{Opioid receptor modulators
Alkaloids
NMDA receptor antagonists
Pyrroloindoles
Mu-opioid receptor agonists