Basic information
- CAS
57-64-7- Standard SMILES
CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN(C)[C@@H]1N2C.O=C(O)c1ccccc1O- InChIKey
HZOTZTANVBDFOF-PBCQUBLHSA-N- Molecular formula
- C15H21N3O2.C7H6O3
- Average molar mass
- 413.5 g/mol
- Monoisotopic mass
- 413.19507096
Overview
Crystal form that turns red on exposure to heat or light. (EPA, 1998)
Names & identifiers
- Preferred name
- (-)-Physostigmine salicylate
- IUPAC
- [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate;2-hydroxybenzoic acid
- English name
- PHYSOSTIGMINE SALICYLATE
- Molecular formula
- C22H27N3O5
- Molecular weight
- 413.47
Names & synonyms
Physostigmine salicylate57-64-7Isopto EserinePhysostigmine monosalicylateNSC-7572752046ZRO9VUPhysostigmini salicylas(-)-Physostigmine salicylateCHEBI:48883DTXSID80883232Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-, mono(2-hydroxybenzoate)ANTICHOLIUM
Show more names
Physostigmine-d3 salicylatePhysostigmine salicylate (6CI)ar-44tl-1380CCRIS 3405EINECS 200-343-8physostolsalicylatePhysostigminsalicylat
RefChem:56715DTXCID501022781200-343-8Eserine salicylatePhysostigmine (salicylate)MLS000028388SMR000058606(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate 2-hydroxybenzoate
Database identifiers
- CAS
57-64-7
Properties
Computed structural properties
- Topological polar surface area
- 102 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 535
Experimental & physicochemical properties
Melting Point365 to 369 °F (EPA, 1998)
Vapor Pressure0.00001 [mm Hg] @25 °C
Physical DescriptionCrystal form that turns red on exposure to heat or light. (EPA, 1998)
Collision Cross Section167.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 181 · 181-183 °C
- storage temp.
- -20 °C · -20°C
- solubility
- 30 mg/ml,DMSO: · DMF: 30 mg/ml,DMSO: 10 mg/ml,Ethanol: 1 mg/ml,PBS (pH 7.2): 1 mg/ml
- pka
- 1.96 · pKa 1.96/8.08(H2O,t =15) (Uncertain)
- form
- Solid
- color
- White to yellow
- biological source
- synthetic
- optical activity
- 20 · [α]20/D -77±2°, c =1% in ethanol
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
This chemical does not meet GHS hazard criteria for 6.5% (3 of 46) of reports.
Danger
H300 (93.5%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Benzoic acid, 2-hydroxy-, compd. with (3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo2,3-bindol-5-yl methylcarbamate (1:1): Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Other Safety InformationIMAP assessments - Benzoic acid, 2-hydroxy-, compound with (3aS-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl methylcarbamate (1:1): Human health tier I assessment
DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits toxic fumes of nitrogen oxides. (EPA, 1998)
Health HazardsThis compound is similar to physostigmine. It is classified as super toxic. The probable oral lethal dose (humans) is less than 5 mg/kg or a taste for a 150 lb. person. It is a cholinesterase inhibitor. (EPA, 1998)
Reactive GroupAmines, Phosphines, and Pyridines
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzoic acid, 2-hydroxy-, compd. with (3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl N-methylcarbamate (1:1): ACTIVE
Applications
UsesPhysostigmine salicylate (Eserine salicylate) is used as bulk pharmaceuticals (parasympathomimetic, cholinergic, ophthalmic, anti-Alzheimer). Product Data Sheet
Usescholinergic, anticholinesterase, miotic
General DescriptionCrystal form that turns red on exposure to heat or light.
General DescriptionThe salicylate ofphysostigmine (eserine salicylate) may be prepared byneutralizing an ethereal solution of the alkaloid with anethereal solution of salicylic acid. Excess salicylic acid isremoved from the precipitated product by washing itwith ether. The salicylate is less deliquescent than thesulfate.Physostigmine salicylate occurs as a white, shining,odorless crystal or white powder that is soluble in water(1:75), alcohol (1:16), or chloroform (1:6) but much lesssoluble in ether (1:250). On prolonged exposure to air andlight, the crystals turn red. The red may be removed bywashing the crystals with alcohol, although this causes lossof the compound as well. Aqueous solutions are neutral orslightly acidic and take on a red coloration after a period.The coloration may be taken as an index of the loss of activityof physostigmine solutions.
Suppliers78 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
Related reactions
2 records
Compound notes
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