Tetrahydroalstonine
Basic information
- CAS
6474-90-4- Standard SMILES
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12- InChIKey
GRTOGORTSDXSFK-DLLGKBFGSA-N- Molecular formula
- C21H24N2O3
- Average molar mass
- 352.4 g/mol
- Monoisotopic mass
- 352.17869263
Overview
Tetrahydroalstonine is a heteropentacyclic compound that is (20alpha)-16,17-didehydro-18-oxayohimban which is substituted at position 16 by a methoxycarbonyl group and at position 19 by a methyl group. It is a metabolite found in several plant species. It has a role as a plant metabolite. It is a methyl ester, a yohimban alkaloid and an organic heteropentacyclic compound. It is a conjugate base of a tetrahydroalstonine(1+).
Names & identifiers
- Preferred name
- Tetrahydroalstonine
- IUPAC
- methyl (1S,15S,16S,20S)-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
- Tetrahydroalstonine
- Molecular formula
- C21H24N2O3
- Molecular weight
- 352.43
Names & synonyms
Tetrahydroalstonine6474-90-4Alstonine, 3,4,5,6-tetrahydro-6U62R2Y5Y2Alstonine, 3,4,5,6-tetrahydro-, (3alpha)-CHEBI:9479DTXSID201020629NSC-72115methyl (1S,15S,16S,20S)-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-carboxylatetetrahydro-alstoninemethyl (1S,15S,16S,20S)-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-carboxylateRefChem:50885
Show more names
ALSTONINE20-alpha)-lphTETRAHYDROALSTONINE(RG)3,4,5,6-tetrahydro-alstonin3α,4,5,6-TetrahydroalstonineAlstonine,3,4,5,6-tetrahydro-,(3.α.)-Tetrahydroalstonine, 98%, from Schefflera octophylla (Lour.) Harmsmethyl (19alpha,20alpha)-16,17-didehydro-19-methyloxayohimban-16-carboxylate(20α)-16,17-Didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid methyl ester
DTXCID301478396229-331-0Alstonine, tetrahydro-EINECS 229-331-0NSC 72115BRN 0097270(-)-Tetrahydroalstoninemethyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylate
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 54.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 606
Physicochemical properties
- Melting point
- 227 °C · 227°C
- Boiling point
- 524 · 524.0±50.0 °C(Predicted)
- Density
- 1.3 · 1.30±0.1 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Solid
- pka
- 18.03 · 18.03±0.60(Predicted)
- color
- Off-white to light yellow
- LogP
- 2.88 · 2.880 (est)
- FDA UNII
- 6 U62R2Y5Y2 · 6U62R2Y5Y2
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 312 · H312-H302
- Precautionary statements
- 280 · P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H312-H302
- Precautionary statements
- P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Applications
UsesTetrahydroalstonine, a indole alkaloid isolated from the fruits of Rhazya stricta, is a selective alpha 2-adrenoceptor antagonist[1][2].
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Tetrahydroalstonine is a heteropentacyclic compound that is (20alpha)-16,17-didehydro-18-oxayohimban which is substituted at position 16 by a methoxycarbonyl group and at position 19 by a methyl group. It is a metabolite found in several plant species. It has a role as a plant metabolite. It is a yohimban alkaloid, an organic heteropentacyclic compound and a methyl ester. It is a conjugate base of a tetrahydroalstonine(1+).
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