Hodgkinsine is an alkaloid found in plants of the Psychotria genus, particularly Psychotria colorata,[1] although it is also found in Psychotria lyciiflora[2] and probably other species in this family,[3] as well as in the related species Calycodendron milnei.[4]
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,[5] both of which are mechanisms of action shared with commonly used painkillers (morphine and ketamine respectively).
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.

(From Wikipedia, the free encyclopedia ; http://en.wikipedia.org/wiki/Hodgkinsine)

See also: http://en.wikipedia.org/wiki/Psychotria_colorata

apparently there are a few opioids related to hodgkinsine, this class of phyto-opioids are known as Pyrrolidinoindolines. Psychotria oleoides and Psychotria lyciiflora contain hodgkinsine as well as meso-chimonanthine, Nb-desmethyl-meso-chimonanthine, and calycosidine. calycosidine is also found in Psychotria rostrata as well as other Psychotria species. the chimonanthine monourethanes are said to have a much stronger binding affinity than hodgkinsine and meso-chimonanthine. chemonanthine and related alkaloids can also be found in Idiospermum australiense.
also wanted to add that hodgkinsine and possibly other opioid pyrrolidinoindolines can also be found in Hodgkinsonia frutescens, Hodgkinsonia ovatiflora, and Calycodendron milnei.
Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-Type alkaloids
Abstract

Hodgkinsine, a trimeric pyrrolidinoindoline type alkaloid, present as a major constituent of Psychotria spp. (Rubiaceae), has shown to produce dose-dependent, naloxone reversible, analgesic effect in thermal models of nociception and in the capsaicin-induced pain. SAR studies have been initiated by synthesizing the three diastereomeric dimers (chimonanthines) (11–13) which were evaluated in vitro and in vivo along with the synthetic intermediates. Strong binding affinities for ? opioid receptors were found for (?)- and (+)-chimonanthine monourethanes (9 and 10), whereas (?)-, (+)- and (meso)-chimonanthine (11–13) and hodgkinsine displayed low affinity. In vivo data have shown that only (+)-chimonanthine (12) and calycosidine resemble the analgesic profile found for hodgkinsine.

(From http://forum.opiophile.org/archive/index.php/t-18145.html)

I'm looking for :
- Journal articles about Hodgkinsine and related
- Experiences Reports
- Potency compared to another opioid

If anyone can find this , it will help me a lot, i find several journal articles but don't have acces to them

Analgesic activity of Psychotria colorata (Willd. ex R. & S.) Muell. Arg. alkaloids - Journal of Ethnopharmacology
Volume 48, Issue 2, October 1995, Pages 77-83 Doi:10.1016/0378-8741(95)01287-N

Opioid-like activity of Psychotria brachypoda - M B Leal and E Elisabet

Verotta L, Orsini F, Sbacchi M, Scheildler MA, Amador TA, Elisabetsky E. Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids. Bioorganic and Medicinal Chemistry. 2002 Jul;10(7):2133-42. PMID 11983509

Kodanko JJ, Hiebert S, Peterson EA, Sung L, Overman LE, de Moura Linck V, Goerck GC, Amador TA, Leal MB, Elisabetsky E. Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity. Journal of Organic Chemistry. 2007 Oct 12;72(21):7909-14. PMID 17887704

Amador TA, Verotta L, Nunes DS, Elisabetsky E. Antinociceptive profile of hodgkinsine. Planta Medica. 2000 Dec;66(:770-2. PMID 11199142

Saad HE, el-Sharkawy SH, Shier WT. Biological activities of pyrrolidinoindoline alkaloids from Calycodendron milnei. Planta Medica. 1995 Aug;61(4):313-6. PMID 7480176

Jannic V, Guéritte F, Laprévote O, Serani L, Martin MT, Sévenet T, Potier P. Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora. Journal of Natural Products. 1999 Jun;62(6):838-43. PMID 10395499

Verotta L, Pilati T, Tatò M, Elisabetsky E, Amador TA, Nunes DS. Pyrrolidinoindoline Alkaloids from Psychotria colorata. Journal of Natural Products. 1998 Mar 27;61(3):392-6. PMID 9548883

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