rescinnamine

{{short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 464380960

| 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

| image = Rescinnamine.svg

| image2 = File:Rescinnamine.png

| width = 300

| tradename = Moderil, Cinnasil, Anaprel

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = By mouth

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| IUPHAR_ligand = 7098

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 24815-24-5

| ATC_prefix = C02

| ATC_suffix = AA01

| ATC_supplemental =

| PubChem = 5280954

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01180

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4444446

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Q6W1F7DJ2D

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00198

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 28572

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1668

| C=35 | H=42 | N=2 | O=9

| smiles = [H] [C@]26C[C@@H](OC(=O)/C=C/c1cc(OC)c(OC)c(OC)c1)[C@H](OC)[C@@H](C(=O)OC)[C@@]2([H])C[C@]5([H])c4[nH]c3cc(OC)ccc3c4CCN5C6

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SZLZWPPUNLXJEA-QEGASFHISA-N

| 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

}}

Rescinnamine, known by the brand names Moderil, Cinnasil, and Anaprel, is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

It is an indoloquinolizine alkaloid similar to reserpine, obtained from Rauvolfia serpentina{{cite journal |vauthors=FIFE R, MACLAURIN JC, WRIGHT JH |title=Rescinnamine in treatment of hypertension in hospital clinic and in general practice |journal=British Medical Journal |volume=2 |issue=5216 |pages=1848–50 |date=December 1960 |pmid=13699407 |pmc=2098607 |doi= 10.1136/bmj.2.5216.1848}} and other species of Rauvolfia.{{cite journal |journal = Planta Med. |year = 1982 |volume = 44 |issue = 2 |pages = 91–3 |title = Alkaloids of Vinca major cv. Variegata. |vauthors = Balsevich J, Constabel F, Kurz WG |pmid = 17402086 |doi=10.1055/s-2007-971409}}