Hodgkinsine

Last updated
Hodgkinsine
Hodgkinsine.svg
Hodgkinsine molecule ball.png
Clinical data
ATC code
  • none
Identifiers
  • (3aR,8bR)-5,8b-bis[(3aR,8bR)-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl]-3- methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole
CAS Number
PubChem CID
ChemSpider
  • none
CompTox Dashboard (EPA)
Chemical and physical data
Formula C33H38N6
Molar mass 518.709 g·mol−1
3D model (JSmol)
  • CN1CC[C@]2([C@@H]1NC3=CC=CC=C32)C4=C5C(=CC=C4)[C@]6(CCN([C@H]6N5)C)[C@@]78CCN([C@@H]7NC9=CC=CC=C89)C
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Hodgkinsine is an alkaloid found in plants of the genus Psychotria , particularly Psychotria colorata , [1] although it is also found in Psychotria lyciiflora [2] and probably other species in this family, [3]

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, [4] both of which are mechanisms of action shared with commonly used painkillers (morphine and ketamine respectively, and which occur concurrently in the clinical analgesics methadone and levorphanol).

Hodgkinsine is a trimer composed of three pyrrolidinoindoline subunits, with the monomer closely resembling another alkaloid eseroline which has similar bioactivity. Due to its complex structure and multiple chiral centres, hodgkinsine has many stereoisomers and significant research has been undertaken to elucidate the structure-activity relationships of the various isomers and synthetic derivatives structurally derived from hodgkinsine. [5] [6] [7]

See also

Related Research Articles

<span class="mw-page-title-main">Epibatidine</span> Toxic chemical from some poison dart frogs

Epibatidine is a chlorinated alkaloid that is secreted by the Ecuadoran frog Epipedobates anthonyi and poison dart frogs from the Ameerega genus. It was discovered by John W. Daly in 1974, but its structure was not fully elucidated until 1992. Whether epibatidine is the first observed example of a chlorinated alkaloid remains controversial, due to challenges in conclusively identifying the compound from the limited samples collected by Daly. By the time that high-resolution spectrometry was used in 1991, there remained less than one milligram of extract from Daly's samples, raising concerns about possible contamination. Samples from other batches of the same species of frog failed to yield epibatidine.

<span class="mw-page-title-main">Voacangine</span> Chemical compound

Voacangine is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.

<span class="mw-page-title-main">Aporphine</span> Chemical compound

Aporphine is an alkaloid with the chemical formula C17H17N. It is the core chemical substructure of the aporphine alkaloids, a subclass of quinoline alkaloids. It can exist in either of two enantiomeric forms, (R)-aporphine and (S)-aporphine.

<span class="mw-page-title-main">7-Hydroxymitragynine</span> Opioid analgesic compound

7-Hydroxymitragynine is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as kratom. It is often referred to as '7-OH'. It was first described in 1994 and is a natural product derived from the mitragynine present in the kratom leaf. It is considered an oxidized derivative and active metabolite of mitragynine. 7-OH binds to opioid receptors like mitragynine, but research suggests that 7-OH binds with greater potency and contributes heavily to the analgesic activity of mitragynine as a metabolite.

<i>Psychotria colorata</i> Species of flowering plant

Psychotria colorata is a species of plant in the family Rubiaceae. It has been documented in an ethnobotanical context among the Ka'apor people of Maranhão, Brazil by Dr. William Balée, the Tulane University anthropologist and historical ecologist:

<span class="mw-page-title-main">Aeruginascin</span> Chemical compound

Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens and Pholiotina cyanopus, and Psilocybe cubensis. Aeruginascin is the N-trimethyl analogue of psilocybin. It is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT3 receptor agonist, but the aeruginascin metabolite 4-HO-TMT shows strong binding at the 5-HT2 receptors similar to psilocin. The first scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989. Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences. This is in contrast to the slight and in some cases extremely dysphoric experiences reported from the accidental ingestion of non aeruginascin containing mushrooms (containing solely psilocybin and psilocin).

<span class="mw-page-title-main">Tebanicline</span> Chemical compound

Tebanicline is a potent synthetic nicotinic (non-opioid) analgesic drug developed by Abbott. It was developed as a less toxic analog of the potent poison dart frog-derived compound epibatidine, which is about 200 times stronger than morphine as an analgesic, but produces extremely dangerous toxic side effects. Like epibatidine, tebanicline showed potent analgesic activity against neuropathic pain in both animal and human trials, but with far less toxicity than its parent compound. It acts as a partial agonist at neuronal nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes.

<span class="mw-page-title-main">Higenamine</span> Chemical compound

Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum, Annona squamosa, and Nelumbo nucifera.

<span class="mw-page-title-main">Pericine</span> Chemical compound

Pericine is one of a number of indole alkaloids found in the tree Picralima nitida, commonly known as akuamma. As with some other alkaloids from this plant such as akuammine, pericine has been shown to bind to mu opioid receptors in vitro, and has an IC50 of 0.6 μmol, within the range of a weak analgesic. It may also have convulsant effects.

<span class="mw-page-title-main">Biosynthesis of cocaine</span>

The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core.

<span class="mw-page-title-main">Arylcyclohexylamine</span> Class of chemical compounds

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

<span class="mw-page-title-main">Psychotridine</span> Chemical compound

Psychotridine is an alkaloid found in some species of the genus Psychotria, namely Psychotria colorata, but also Psychotria forsteriana, Psychotria lyciiflora, Psychotria oleoides, and Psychotria beccarioides. Psychotridine has analgesic effects and dose-dependently inhibits dizocilpine binding to cortical membranes in vitro, suggesting that it acts as a non-competitive NMDA receptor antagonist.

<span class="mw-page-title-main">Jatrorrhizine</span> Chemical compound

Jatrorrhizine is a protoberberine alkaloid found in some plant species, such as Enantia chlorantha (Annonaceae). Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, and yatrorizine.

<span class="mw-page-title-main">Matrine</span> Chemical compound

Matrine is an alkaloid found in plants from the genus Sophora. It has a variety of pharmacological effects, including anti-cancer effects, as well as κ-opioid and μ-opioid receptor agonism.

<span class="mw-page-title-main">Taspine</span> Chemical compound

Taspine is an alkaloid which acts as a potent acetylcholinesterase inhibitor and cicatrizant. It is found in various plants including Magnolia x soulangeana and Croton lechleri.

<span class="mw-page-title-main">Akuammicine</span> Alkaloid

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.

<span class="mw-page-title-main">Dicentrine</span> Chemical compound

Dicentrine is an aporphinic alkaloid found in several plant species, mainly from family Lauraceae, including Lindera megaphylla. At high doses, dicentrine shows antinociceptive activity in a mouse model of pain. It probably acts via a TRPA1-dependent mechanism.

<span class="mw-page-title-main">Incarvillateine</span> Chemical compound

Incarvillateine is a complex monoterpene alkaloid that is a derivative of α-truxillic acid. It can be isolated from the plant genus Incarvillea.

<span class="mw-page-title-main">Speciociliatine</span> Chemical compound

Speciociliatine is a major alkaloid of the plant Mitragyna speciosa, commonly known as kratom. It is a stereoisomer of Mitragynine and constitutes 0.00156 - 2.9% of the dried leaf material.

References

  1. Verotta L, Pilati T, Tatò M, Elisabetsky E, Amador TA, Nunes DS (March 1998). "Pyrrolidinoindoline Alkaloids from Psychotria colorata1". Journal of Natural Products. 61 (3): 392–6. doi:10.1021/np9701642. PMID   9548883.
  2. Jannic V, Guéritte F, Laprévote O, Serani L, Martin MT, Sévenet T, Potier P (June 1999). "Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora". Journal of Natural Products. 62 (6): 838–43. doi:10.1021/np9805387. PMID   10395499.
  3. Saad HE, el-Sharkawy SH, Shier WT (August 1995). "Biological activities of pyrrolidinoindoline alkaloids from Calycodendron milnei". Planta Medica. 61 (4): 313–6. doi:10.1055/s-2006-958090. PMID   7480176.
  4. Amador TA, Verotta L, Nunes DS, Elisabetsky E (December 2000). "Antinociceptive profile of hodgkinsine". Planta Medica. 66 (8): 770–2. doi:10.1055/s-2000-9604. PMID   11199142.
  5. Verotta L, Orsini F, Sbacchi M, Scheildler MA, Amador TA, Elisabetsky E (July 2002). "Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids". Bioorganic & Medicinal Chemistry. 10 (7): 2133–42. doi:10.1016/s0968-0896(02)00078-0. PMID   11983509.
  6. Kodanko JJ, Overman LE (June 2003). "Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B". Angewandte Chemie. 42 (22): 2528–31. doi:10.1002/anie.200351261. PMID   12800178.
  7. Kodanko JJ, Hiebert S, Peterson EA, Sung L, Overman LE, de Moura Linck V, et al. (October 2007). "Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity". The Journal of Organic Chemistry. 72 (21): 7909–14. doi:10.1021/jo7013643. PMID   17887704.