Corynanthine

Chemical compound
  • none
Legal statusLegal status
  • In general: uncontrolled
Identifiers
  • (16β,17α)-17-hydroxy-yohimban-16-carboxylic acid methyl ester
CAS Number
  • 483-10-3
PubChem CID
  • 92766
IUPHAR/BPS
  • 5345
ChemSpider
  • 83744
UNII
  • F5Z7C9RK8U
ECHA InfoCard100.006.901 Edit this at WikidataChemical and physical dataFormulaC21H26N2O3Molar mass354.450 g·mol−13D model (JSmol)
  • Interactive image
  • O=C(OC)[C@H]5[C@H]4C[C@H]3c2[nH]c1ccccc1c2CCN3C[C@@H]4CC[C@@H]5O

Corynanthine, also known as rauhimbine, is an alkaloid found in the Rauvolfia and Corynanthe (including Pausinystalia) 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 the α2-adrenergic receptor over the α1-adrenergic receptor.[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 Rauvolfia extracts. Like yohimbine and rauwolscine, corynanthine has also been shown to possess some activity at serotonin receptors.[5]

See also

References

  1. ^ PHILLIPS DD, CHADHA MS (September 1955). "The alkaloids of Rauwolfia serpentina Benth". Journal of the 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". Pharmaceutical Biology. doi:10.1076/phbi.39.3.239.5923. S2CID 85168336.
  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. S2CID 24276613.
  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. S2CID 19770424.
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