Rauwolscine

Rauwolscine
Rauwolscine_3D_BS
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 17α-hydroxy-20α-yohimban-16β-carboxylic acid methyl ester
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.553 Edit this at Wikidata
Chemical and physical data
FormulaC21H26N2O3
Molar mass354.450 g·mol−1
  • InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15+,17+,18+,19+/m1/s1 checkY
  • Key:BLGXFZZNTVWLAY-DIRVCLHFSA-N checkY
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Rauwolscine, also known as isoyohimbine, α-yohimbine, and corynanthidine, is an alkaloid found in various species within the genera Rauvolfia and Corynanthe (including Pausinystalia).[1] It is a stereoisomer of yohimbine.[1] Rauwolscine is a central nervous system stimulant, a local anesthetic and a vague aphrodisiac.[1]

Rauwolscine acts predominantly as a α2-adrenergic receptor antagonist.[2][3] It has also been shown to function as a 5-HT1A receptor partial agonist and 5-HT2A and 5-HT2B receptor antagonist.[4][5][6]

  1. ^ a b c Kohli JD, De NN (June 1956). "Pharmacological action of rauwolscine". Nature. 177 (4521): 1182. Bibcode:1956Natur.177.1182K. doi:10.1038/1771182a0. PMID 13334509. S2CID 4212268.
  2. ^ Perry BD, U'Prichard DC (December 1981). "[3H]rauwolscine (alpha-yohimbine): a specific antagonist radioligand for brain alpha 2-adrenergic receptors". European Journal of Pharmacology. 76 (4): 461–464. doi:10.1016/0014-2999(81)90123-0. PMID 6276200.
  3. ^ Qin K, Sethi PR, Lambert NA (August 2008). "Abundance and stability of complexes containing inactive G protein-coupled receptors and G proteins". FASEB Journal. 22 (8): 2920–2927. doi:10.1096/fj.08-105775. PMC 2493464. PMID 18434433.
  4. ^ Arthur JM, Casañas SJ, Raymond JR (June 1993). "Partial agonist properties of rauwolscine and yohimbine for the inhibition of adenylyl cyclase by recombinant human 5-HT1A receptors". Biochemical Pharmacology. 45 (11): 2337–2341. doi:10.1016/0006-2952(93)90208-E. PMID 8517875.
  5. ^ Kaumann AJ (June 1983). "Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 323 (2): 149–154. doi:10.1007/BF00634263. PMID 6136920. S2CID 23251900.
  6. ^ Wainscott DB, Sasso DA, Kursar JD, Baez M, Lucaites VL, Nelson DL (January 1998). "[3H]Rauwolscine: an antagonist radioligand for the cloned human 5-hydroxytryptamine2b (5-HT2B) receptor". Naunyn-Schmiedeberg's Archives of Pharmacology. 357 (1): 17–24. doi:10.1007/PL00005133. PMID 9459568. S2CID 28910390. Archived from the original on 2001-09-11.