Rescinnamine - Wikipedia

Rescinnamine
Clinical data


Trade names	Moderil, Cinnasil, Anaprel
Other names	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
Routes of administration	By mouth
ATC code	C02AA01 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
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
CAS Number	24815-24-5^Y
PubChem CID	5280954
IUPHAR/BPS	7098
DrugBank	DB01180^Y
ChemSpider	4444446^Y
UNII	Q6W1F7DJ2D
KEGG	D00198^Y
ChEBI	CHEBI:28572^Y
ChEMBL	ChEMBL1668^Y
CompTox Dashboard (EPA)	DTXSID3023554
ECHA InfoCard	100.042.232
Chemical and physical data
Formula	C₃₅H₄₂N₂O₉
Molar mass	634.726 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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^Y Key:SZLZWPPUNLXJEA-QEGASFHISA-N^Y
(verify)

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^[1] and other species of Rauvolfia.^[2]

References

[edit]

^ 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.
^ 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.

v t e Antihypertensive drugs acting on the renin–angiotensin system (C09)
ACE inhibitors ("-pril")	Sulfhydryl-containing: Captopril Rentiapril Zofenopril (+nebivolol) Dicarboxylate-containing: Enalapril^# (+lercanidipine, +nitrendipine) Benazepril (+amlodipine, +pimobendan) Cilazapril Delapril (+manidipine) Imidapril Lisinopril (+amlodipine, +HCT) Moexipril Perindopril (+amlodipine, +bisoprolol, +indapamide, +amlodipine and indapamide, +bisoprolol and amlodipine, +bisoprolol, amlodipine, and indapamide) Quinapril (+HCT) Ramipril (+amlodipine, +amlodipine and HCT, +bisoprolol, +felodipine) Spirapril Temocapril Trandolapril (+verapamil) Phosphonate-containing: Ceronapril Fosinopril (+HCT) Other/ungrouped: Alacepril
AIIRAs ("-sartan")	Azilsartan Candesartan (+amlodipine, +amlodipine and HCT) Eprosartan Fimasartan Irbesartan (+amlodipine, +amlodipine and HCT, +HCT) Losartan (+amlodipine, +HCT) Olmesartan (+amlodipine, +amlodipine and HCT, +HCT) Tasosartan^§ Telmisartan (+amlodipine, +amlodipine and HCT, +HCT) Valsartan (+aliskiren, +amlodipine, +amlodipine and HCT, +HCT, +lercanidipine, +nebivolol, +sacubitril)
Renin inhibitors ("-kiren")	Aliskiren (+amlodipine, +HCT, +amlodipine and HCT) Remikiren^§
Dual ACE/NEP inhibitors	Gemopatrilat Ilepatril Omapatrilat Sampatrilat
Neprilysin inhibitors	Sacubitril (+valsartan)
Other	Sparsentan
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Angiotensin receptor modulators

ATR

Propeptides: Angiotensinogen
Angiotensin I

Combinations:

v t e Tryptamines
Tryptamines	1-Methyl-T 1-Methylpsilocin 2-HO-NMT 2-Me-DET 2-Methyl-5-HT 2,N,N-TMT 4,5-DHP-DMT 4-AcO-DALT 4-AcO-DET 4-AcO-DiPT 4-AcO-DPT 4-AcO-EPT 4-AcO-MALT 4-AcO-MET 4-AcO-MiPT 4-AcO-NMT 4-AcO-TMT 4-F-5-MeO-DMT 4-Fluoro-T 4-HO-5-MeO-DMT 4-HO-DALT 4-HO-DBT 4-HO-DET 4-HO-DiPT 4-HO-DPT 4-HO-DSBT 4-HO-EPT 4-HO-MALT 4-HO-MET 4-HO-McPT 4-HO-McPeT 4-HO-MiPT 4-HO-MPT 4-HO-MsBT 4-HO-NALT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-HO-TMT 4-HT 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-MET 5-Fluoro-T 5-HO-DiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT 5-MeO-pyr-T 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine) 5-MeO-T-NBOMe 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-MT-NB3OMe 5-NOT 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-DHT 5,7-DHT 6-Fluoro-DMT 6-Fluoro-T 6-MeO-DMT 6-MeO-T 6-Methyl-T 7-Chloro-T 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Aeruginascin (4-PO-TMT) AGH-107 AGH-192 AH-494 ALiPT Alpertine Baeocystin (4-PO-NMT) Benzotript (4-chlorobenzoyl-L-tryptophan) Bufotenidine (5-HTQ) Bufotenin (5-HO-DMT) Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EMDT EPT Ethocybin (4-PO-DET) FGIN-127 FGIN-143 FT-104 HIOC Idalopirdine Indolylethylfentanyl Indorenate Iprocin (4-HO-DiPT) Isamide Lespedamine MBT MET Milipertine Miprocin (4-HO-MiPT) MiPT MPT MS-245 MSBT N-Feruloylserotonin (moschamine) NET/NETP NiPT NMT Norbaeocystin (4-PO-T) NTBT O-4310 O-Pivalylbufotenine Oxypertine PiPT Psilacetin (O-acetylpsilocin; 4-AcO-DMT) Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Pyr-T RS134-49 Serotonin (5-HT) Solypertine ST-1936 Tryptamine (T) Tryptophan Yuremamine Z2876442907
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301
α-Alkyltryptamines	2,α-DMT 4-HO-αMT 4-HO-MPMI (lucigenol) 4-Me-αET 4-Me-αMT 5-Chloro-αET 5-Chloro-αMT 5-Ethoxy-αMT 5-Fluoro-αET 5-Fluoro-αMT 5-iPrO-αMT 5-MeO-α,N,N-TMT 5-MeO-αET 5-MeO-αMT 5-MeO-MPMI 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Methyl-αET α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT) α-Methyltryptophan (αMTP) α,N-DMT (N-methyl-αMT) α,N,N-TMT α,N,O-TMS αET (etryptamine) αMT AL-37350A (4,5-DHP-αMT) BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT BNC-210 BW-723C86 CP-135807 IPAP (α,N-DPT) MPMI
Triptans	Almotriptan Donitriptan Eletriptan Frovatriptan L-694247 Rizatriptan Sumatriptan Zolmitriptan
Cyclized tryptamines	Bay R 1531 Ciclindole Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD) Flucindole Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH, 9-Me-BC, β-carboline (norharman), harmaline, harmalol, harmane, harmine, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids and related (e.g., DM-506 (ibogaminalog), ibogaine, ibogamine, noribogaine, tabernanthalog, tabernanthine) LY-266,097 Metralindole NDTDI PHA-57378 PNU-22394 PNU-181731 RU-28306 Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine)
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT AAZ-A-154 (DLX-001) isoAMT isoDMT Isotryptamine (isoT) PNU-181731 Ro60-0175
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT AAZ-A-154 AL-34662 AL-38022A Benzofurans (e.g., 3-APB, 5-MeO-DiBF, BPAP, dimemebfe, mebfap) BRL-54443 CP-94253 EMD-386088 I-32 IAL Latrepirdine LY-367265 Non-tryptamine triptans (e.g., avitriptan, LY-334370, naratriptan) Pirlindole (R)-69 (3IQ) Ro60-0213 RU-24,969 Sertindole SN-22 Tepirindole Tetrindole VER-3323 VU6067416 YM-348

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