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51-34-3

Basic Information
CAS No.: 51-34-3
Name: Scopolamine
Article Data: 21
Molecular Structure:
Molecular Structure of 51-34-3 (Scopolamine)
Formula: C17H21NO4
Molecular Weight: 303.35
Synonyms: (-)-Hyoscine;(-)-Scopolamine;6,7-Epoxytropinetropate;9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-tropate;Hyoscine;Scopine (-)-tropate;l-Scopolamine;
EINECS: 200-090-3
Density: 1.313 g/cm3
Melting Point: 59 °C
Boiling Point: 460.313 °C at 760 mmHg
Flash Point: 232.189 °C
Solubility: 95g/L(15 oC)
Appearance: White crystalline powder
Hazard Symbols: VeryT+
Risk Codes: 26/27/28
Safety: 25-45
PSA: 62.30000
LogP: 0.85600
Synthetic route
605-65-2

5-(dimethylamino)naphth-1-ylsulfonyl chloride

51-34-3

(S)-3-hydroxy-2-phenyl-propionic acid 9-methyl-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7t-yl ester

64492-75-7

(S)-3-hydroxy-2-phenyl-propionic acid 9-(5-dimethylamino-naphthalene-1-sulfonyl)-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7t-yl ester

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History

Scopolamine is extracted from plant by German chemists in 1881 .Scopolamine was one of the active ingredients in Asthmador,It is claimed to combat asthma and bronchitis in the 1950s and 60's.It was used from the 1940s to the 1960s to put mothers in labor into a kind of "twilight sleep" that did not stop pain, but merely eliminated the memory of pain by attacking the brain functions responsible for self-awareness and self-control. Often, it can cause a kind of psychosis, followed by post-traumatic stress-like memories in thousands of new mothers.Before November 1990 Scopolamine was an ingredient used in some over-the-counter sleep aids  in the United States.

Consensus Reports

EPA Genetic Toxicology Program.

Specification

The Benzeneacetic acid, a-(hydroxymethyl)-, (1a,2b,4b,5a,7b)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, (aS)-, with the CAS registry number 51-34-3, is also known as 6beta,7beta-Epoxy-1alpha,5alpha-tropan-3alpha-ol. Its EINECS number is 200-090-3. This chemical's molecular formula is C17H21NO4 and molecular weight is 303.35. What's more, its systematic name is (1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate. Its classification codes are: (1)Adjuvants, anesthesia; (2)Autonomic Agents; (3)Central Nervous System Agents; (4)Cholinergic Agents; (5)Cholinergic Antagonists; (6)Drug / Therapeutic Agent; (7)Human Data; (8)Muscarinic antagonists; (9)Mutation data; (10)Mydriatics; (11)Neurotransmitter Agents; (12)Peripheral Nervous System Agents; (13)Reproductive Effect. This chemical can be administered orally, subcutaneously, opthalmically and intravenously, as well as via a transdermal patch. It is a tropane alkaloid drug with muscarinic antagonist effects. It has a number of uses in medicine.

Physical properties of Benzeneacetic acid, a-(hydroxymethyl)-, (1a,2b,4b,5a,7b)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-ylester, (aS)- are: (1)ACD/LogP: 0.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.65; (4)ACD/LogD (pH 7.4): 0.05; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 12.15; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 62.3 Å2; (13)Index of Refraction: 1.614; (14)Molar Refractivity: 80.443 cm3; (15)Molar Volume: 230.953 cm3; (16)Polarizability: 31.89×10-24cm3; (17)Surface Tension: 56.39 dyne/cm; (18)Density: 1.313 g/cm3; (19)Flash Point: 232.189 °C; (20)Enthalpy of Vaporization: 75.966 kJ/mol; (21)Boiling Point: 460.313 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic by inhalation, in contact with skin and if swallowed. You must avoid contact with eyes. In case of accident or if you feel unwell, you need seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@H]3N(C)[C@@H](C2)[C@@H]4O[C@H]34
(2)Std. InChI: InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
(3)Std. InChIKey: STECJAGHUSJQJN-FWXGHANASA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intramuscular 4ug/kg (0.004mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
"Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents," National Research Council, 3 vols., Washington, DC, National Academy Press, 1982-85Vol. 1, Pg. L1, 1982.
human TDLo subcutaneous 2ug/kg (0.002mg/kg) BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT
Journal of Pharmacology and Experimental Therapeutics. Vol. 137, Pg. 133, 1962.
man TDLo intramuscular 24ug/kg (0.024mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 32, Pg. 250, 1973.
man TDLo subcutaneous 14ug/kg (0.014mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: ATAXIA
American Journal of Psychiatry. Vol. 141, Pg. 1010, 1984.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: IRRITABILITY
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1727, 1971.
mouse LD50 intravenous 100mg/kg (100mg/kg)   Journal of Medicinal Chemistry. Vol. 26, Pg. 1772, 1983.
mouse LD50 oral 1275mg/kg (1275mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: REGIDITY
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 134, Pg. 255, 1961.
mouse LD50 subcutaneous 1700mg/kg (1700mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 56, Pg. 85, 1936.
rabbit LDLo intravenous 50mg/kg (50mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit LDLo subcutaneous 75mg/kg (75mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 oral 2650mg/kg (2650mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C272, 1991.
women TDLo subcutaneous 13ug/kg (0.013mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: ATAXIA
American Journal of Psychiatry. Vol. 141, Pg. 1010, 1984.