Benzeneacetic acid, alpha-hydroxy-alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))-
Basic information
- CAS
52646-92-1- Standard SMILES
CN1[C@@H]2CC(OC(=O)[C@@](O)(CO)c3ccccc3)C[C@H]1[C@@H]1O[C@@H]12- InChIKey
JEJREKXHLFEVHN-VJDHNPKBSA-N- Molecular formula
- C17H21NO5
- Average molar mass
- 319.4 g/mol
- Monoisotopic mass
- 319.14197277
Overview
Benzeneacetic acid, alpha-hydroxy-alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))- has been reported in Anisodus tanguticus with data available.
Names & identifiers
- Preferred name
- Benzeneacetic acid, alpha-hydroxy-alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))-
- IUPAC
- [(1S,2S,4R,5R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-2,3-dihydroxy-2-phenylpropanoate
- English name
- Anisodine
- Molecular formula
- C17H21NO5
- Molecular weight
- 319.35
Names & synonyms
Benzeneacetic acid, alpha-hydroxy-alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))-RefChem:1078345anisodine52646-92-1Z75256J75J[(1S,2S,4R,5R)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-2,3-dihydroxy-2-phenylpropanoateUNII-Z75256J75JDATURAMINEANISODINE [WHO-DD]orb1740330CHEMBL5095784SCHEMBL28137855
Show more names
ANISODINE USP/EP/BP(αS)-α-Hydroxy-α-(hydroxymethyl)benzeneacetic acid (1R,2R,4S,5S,7α)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nona-7-yl esterBenzeneacetic acid, α-hydroxy-α-(hydroxymethyl)-, (1α,2β,4β,5α,7β)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (αS)-
.ALPHA.-HYDROXYSCOPOLAMINEDTXSID20967080T69150(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]nonan-7-yl (2S)-2,3-dihydroxy-2-phenylpropanoate[(1R,2R,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-2,3-dihydroxy-2-phenylpropanoate6.BETA.,7.BETA.-EPOXY-1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-YL (-)-2,3-DIHYDROXY-2-PHENYLPROPIONATEBENZENEACETIC ACID, .ALPHA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-, 9-METHYL-3-OXA-9-AZATRICYCLO(3.3.1.02,4)NON-7-YL ESTER, (7(S)-(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.))-
Database identifiers
- CAS
52646-92-1- PubChem CID
- 11616712
- DTXSID
DTXSID20967080- ChEMBL
CHEMBL5095784- UNII
- Z75256J75J
- Nikkaji
- J39.182D
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 82.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 462
Physicochemical properties
- Melting point
- 199.5 · 199.5-200 °C
- Boiling point
- 495 · 495.0±45.0 °C(Predicted)
- Density
- 1.39 · 1.39±0.1 g/cm3(Predicted)
- pka
- 11.34 · 11.34±0.29(Predicted)
- FDA UNII
- 75256 J75J · Z75256J75J
Chemistry & industry
Applications
DescriptionAnisodine is isolated from the roots of the plant Solanaceae Anisodus tanguticus (Maxim.) Pasch. (Scopolia tangutica Maxim.), which has a common name of Zhang-Liu-Shen, growing at the plateau with an altitude of 1700–4300m and richly distributed in Tibet, Sichuan, Qinghai, Gansu, and other provinces in China.
HistoryAnisodine hydrobromide was an originally created new drug in China. It was separated from the herbal medicine Anisodus tanguticus from Qinghai province. In the early 1960s, Anisodus tanguticus was given the common name of Zhang-Liu-Shenin Qinghai province, similar to the common name Zhang Liu of Radix Phytolaccae. As a result, the root was misused as Radix Phytolaccae until the occurrence of atropine poisoning symptoms. Histological identification found that it is Anisodus tanguticus (Maxim.) Pasch, not Radix Phytolaccae. In order to make full use of the wild plant’s resources and develop the products of henbane drugs in China, the Chinese Academy of Medical Sciences carried out the systemic research on the plant .
Related reactions
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Compound notes
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