Rescinnamine

Rescinnamine

Systematic (IUPAC) name
methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}yohimban-16-carboxylate
Clinical data
Routes of administration	oral
Legal status	℞ (Prescription only)
Identifiers
CAS Number	24815-24-5
ATC code	C02AA01 (WHO)
PubChem	CID 5280954
IUPHAR/BPS	7098
DrugBank	DB01180
ChemSpider	4444446
UNII	Q6W1F7DJ2D
KEGG	D00198
ChEBI	CHEBI:28572
ChEMBL	CHEMBL1668
Synonyms	methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^2,10.0^4,9.0^15,20]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
Chemical data
Formula	C35H42N2O9
Molar mass	634.716 g/mol
SMILES O=C(OC)[C@H]6[C@H]4C[C@@H]3c2nc1cc(OC)ccc1c2CCN3C[C@H]4C[C@@H](OC(=O)\C=C\c5cc(OC)c(OC)c(OC)c5)[C@@H]6OC
InChI InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1 Key:SZLZWPPUNLXJEA-QEGASFHISA-N
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Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

It is an vinca alkaloid obtained from Rauwolfia serpentina^[1] and other species of Rauwolfia.^[2]

Brand names

Moderil, Cinnasil, Anaprel

References

1. FIFE R, MACLAURIN JC, WRIGHT JH (December 1960). "Rescinnamine in treatment of hypertension in hospital clinic and in general practice". British Medical Journal 2 (5216): 1848–50. doi:10.1136/bmj.2.5216.1848. PMC 2098607. PMID 13699407.
2. Balsevich J, Constabel F, Kurz WG. (1982). "Alkaloids of Vinca major cv. Variegata.". Planta Med. 44 (2): 91–3. doi:10.1055/s-2007-971409. PMID 17402086.