Rhynchophylline

Rhynchophylline

Rhynchophylline
Systematic (IUPAC) name
methyl (7β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan- 17-oate
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code None
PubChem
ChEMBL  N
Synonyms methyl (E)-2-[(3R,6'R,7'S,8'aS)- 6'-ethyl- 2-oxospiro[1H-indole-3,1'- 3,5,6,7,8,8a-hexahydro- 2H-indolizine]- 7'-yl]- 3-methoxyprop- 2-enoate
Chemical data
Formula C22H28N2O4 
Mol. mass 384.46872 g/mol
 N   

Rhynchophylline is an alkaloid found in certain Uncaria species (Rubiaceae), notably Uncaria rhynchophylla[1] and Uncaria tomentosa.[2] It is a non-competitive NMDA antagonist (IC50 = 43.2 microM) and calcium channel blocker.[3][4] It also occurs naturally in the leaves of the Mitragyna speciosa (Kratom) tree (also a Rubiaceae), native to Thailand.[5]

References

  1. ^ Shi JS, Yu JX, Chen XP, Xu RX (2003). Alkaloids, Rhynchophylline and Isorhynchophylline"Uncaria"Pharmacological Actions of (pdf). Acta Pharmacologica Sinica 24 (2): 97–101.  
  2. ^ Mohamed AF, Matsumoto K, Tabata K, Takayama H, Kitajima M, Watanabe H (2000). "Effects of Uncaria tomentosa Total Alkaloid and its Components on Experimental Amnesia in Mice: Elucidation Using the Passive Avoidance Test". Journal of Pharmacy and Pharmacology 52 (12): 1553–1561.  
  3. ^ Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H (2002). "Rhynchophylline and Isorhynchophylline Inhibit NMDA Receptors Expressed in Xenopus Oocytes". European Journal of Pharmacology 455 (1): 27–34.  
  4. ^ Kang TH, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H, Matsumoto K (2004). "Protective Effect of Rhynchophylline and Isorhynchophylline on in vitro Ischemia-Induced Neuronal Damage in the Hippocampus: Putative Neurotransmitter Receptors Involved in their Action". Life Sciences 76 (3): 331–343.  
  5. ^ Microgram Bulletin (March 2006). "DEA; Special Intelligence Brief - Kratom (Mitragyna speciosa)". DEA Microgram Bulletin.