Reserpiline
Basic information
- CAS
131-02-2- Standard SMILES
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)[C@H]3C[C@H]12- InChIKey
FGWJRZQNNZVCHR-BCRCDCHUSA-N- Molecular formula
- C23H28N2O5
- Average molar mass
- 412.5 g/mol
- Monoisotopic mass
- 412.199822
Overview
Reserpiline is a yohimban alkaloid.
Names & identifiers
- Preferred name
- Reserpiline
- IUPAC
- methyl (1R,15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
- English name
- methyl (3beta,19alpha,20alpha)-16,17-didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylate
- Molecular formula
- C23H28N2O5
- Molecular weight
- 412.48
Names & synonyms
Reserpiline131-02-2ElliptamineReserpilin(-)-ReserpilineUNII-C0N6EP99UKEINECS 205-005-3C0N6EP99UKRESERPILINE [MI]methyl (1R,15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylateRESERPILINE [WHO-DD]Methyl 16,17-didehydro-10,11-dimethoxy-19alpha-methyl-18-oxa-3beta,20alpha-yohimban-16-carboxylat
Show more names
Methyl (3?,19?,20?)-16,17-didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylate(3β,20α)-16,17-Didehydro-19α-methyl-10,11-dimethoxy-18-oxayohimban-16-carboxylic acid methyl ester(3β,20α)-16,17-Didehydro-10,11-dimethoxy-19α-methyl-18-oxayohimban-16-carboxylic acid methyl ester4H-Indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylic acid, 4a,5,7,8,13,13b,14,14a-octahydro-10,11-dimethoxy-4-methyl-, methyl ester, (4S,4aS,13bR,14aS)-
Oxayohimban-16-carboxylic acid, 16,17-didehydro-10,11-dimethoxy-19-methyl-, methyl ester, (3-beta,19-alpha,20-alpha)-4H-INDOLO(2,3-A)PYRANO(3,4-G)QUINOLIZINE-1-CARBOXYLIC ACID, 4A,5,7,8,13,13B,14,14A-OCTAHYDRO-10,11-DIMETHOXY-4-METHYL-, METHYL ESTER, (4S,4AS,13BR,14AS)-methyl (1R,15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-2(10),4,6,8,18-pentaene-19-carboxylateMethyl 6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo(11.8.0.0,.0,.0,)henicosa-2(10),4,6,8,18-pentaene-19-carboxylic acidMethyl 6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4,6,8,18-pentaene-19-carboxylic acidRefChem:178894205-005-3FGWJRZQNNZVCHR-UHFFFAOYSA-N
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 73 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 699
Physicochemical properties
- alpha
- 20 · D20 -38° (ethanol); -14° (c = 1.5 in pyridine); -12° (c = 1.7 in chloroform)
- Boiling point
- 180 · 180-185 °C(Press: 0.01 Torr)
- Density
- 1.31 · 1.31±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- pka
- 17.95 · 17.95±0.60(Predicted)
- form
- A solid
- FDA UNII
- 0 N6EP99UK · C0N6EP99UK
- RIDADR
- 1544 · 1544
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Toxicity
- 19 mg/kg · guinea pig,LDLo,intravenous,19mg/kg (19mg/kg),Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 600, 1973.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- ridadr
- 1544
- Toxicity
- guinea pig,LDLo,intravenous,19mg/kg (19mg/kg),Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 600, 1973.
- hazard_class
- 6.1(b)
- packing_group
- III
Chemistry & industry
Applications
DescriptionAn amorphous alkaloid present in Rauwolfia canescens and R. serpentina, the alkaloid forms several crystalline salts and derivatives including the hydrochloride, m.p. 205-7°C; [α]24D - 40° (c 0.44, EtOH); the tartrate, m.p. 190- 2°C; [α]20D - 50° (c 1.0, H20); the oxalate, m.p. 252°C; [α]20D - 4° (c 0.2, aqueous EtOH); the picrate, m.p. 173°C and the di-p-toluyl-L-tartrate, m.p. 194- 5° C (dec.).
Additional notes
DefinitionChEBI: Reserpiline is a yohimban alkaloid.
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