Corynanthine

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Corynanthine
Corynanthine.png
Systematic (IUPAC) name
(16β,17α)-17-hydroxy-yohimban-16-carboxylic acid methyl ester
Clinical data
  • Uncontrolled
Oral
Identifiers
483-10-3
None
PubChem CID 92766
ChemSpider 83744
Chemical data
Formula C21H26N2O3
354.44 g/mol

Corynanthine, also known as rauhimbine, is an alkaloid found in the Rauwolfia and Pausinystalia (formerly known as Corynanthe) genera of plants.[1][2] It is one of the two diastereoisomers of yohimbine, the other being rauwolscine.[3][4] It is also related to ajmalicine.

Corynanthine acts as an α1-adrenergic and α2-adrenergic receptor antagonist with approximately 10-fold selectivity for the former site over the latter.[3][4] This is in contrast to yohimbine and rauwolscine which have around 30-fold higher affinity for α2-adrenergic over α1-adrenergic.[3][4] As a result, corynanthine is not a stimulant (or an aphrodisiac for that matter), but a depressant, and likely plays a role in the antihypertensive properties of Rauwolfia extracts. Like yohimbine and rauwolscine, corynanthine has also been shown to possess some activity at serotonin receptors.[5]

See also[edit]

References[edit]

  1. ^ PHILLIPS DD, CHADHA MS (September 1955). "The alkaloids of Rauwolfia serpentina Benth". Journal of the American Pharmaceutical Association. American Pharmaceutical Association 44 (9): 553–67. doi:10.1002/jps.3030440912. PMID 13251932. 
  2. ^ "Alkaloids from Rauvolfia canescens; Pharmaceutical Biology - 39(3):Pages 239-240 - Informa Healthcare". 
  3. ^ a b c Shepperson NB, Duval N, Massingham R, Langer SZ (November 1981). "Pre- and postsynaptic alpha adrenoceptor selectivity studies with yohimbine and its two diastereoisomers rauwolscine and corynanthine in the anesthetized dog". The Journal of Pharmacology and Experimental Therapeutics 219 (2): 540–6. PMID 6270312. 
  4. ^ a b c Doxey JC, Lane AC, Roach AG, Virdee NK (February 1984). "Comparison of the alpha-adrenoceptor antagonist profiles of idazoxan (RX 781094), yohimbine, rauwolscine and corynanthine". Naunyn-Schmiedeberg's Archives of Pharmacology 325 (2): 136–44. doi:10.1007/bf00506193. PMID 6144048. 
  5. ^ Feuerstein TJ, Hertting G, Jackisch R (May 1985). "Endogenous noradrenaline as modulator of hippocampal serotonin (5-HT)-release. Dual effects of yohimbine, rauwolscine and corynanthine as alpha-adrenoceptor antagonists and 5-HT-receptor agonists". Naunyn-Schmiedeberg's Archives of Pharmacology 329 (3): 216–21. doi:10.1007/bf00501871. PMID 2991775.