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Tropine

Names

[ CAS No. ]:
120-29-6

[ Name ]:
Tropine

[Synonym ]:
(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Tropine
endo-Tropanol
TROPAN-3ALPHA-OL
3alpha-Tropanol
8-Azabicyclo[3.2.1]octan-3-ol, 8-methyl-
EINECS 204-384-2
MFCD00005551
8-Azabicyclo[3.2.1]octan-3-ol, 8-methyl-, (1R,5S)-
endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
tropinol
3-TROPANOL
TROPANOL

Biological Activity

[Description]:

Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Neurological Disease

[References]

[1]. Grynkiewicz G, et al. Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs.Pharmacol Rep. 2008 Jul-Aug;60(4):439-63.

[2]. Richter U, et al. Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.J Exp Bot. 2005 Feb;56(412):645-52. Epub 2005 Jan 10.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
233.0±0.0 °C at 760 mmHg

[ Melting Point ]:
50-60 °C(lit.)

[ Molecular Formula ]:
C8H15NO

[ Molecular Weight ]:
141.211

[ Flash Point ]:
112.5±14.5 °C

[ Exact Mass ]:
141.115356

[ PSA ]:
23.47000

[ LogP ]:
-0.10

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.526

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
100 g/L (20 ºC)

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YM3875000
CHEMICAL NAME :
1-alpha-H,5-alpha-H-Tropan-3-alpha-ol
CAS REGISTRY NUMBER :
120-29-6
BEILSTEIN REFERENCE NO. :
0080188
LAST UPDATED :
199701
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C8-H15-N-O
MOLECULAR WEIGHT :
141.24

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
139 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ANCPAC Annales de Chimie. (Masson et Cie, Paris, France) V.9-15, 1914-77. Volume(issue)/page/year: 7,537,1962
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ANCPAC Annales de Chimie. (Masson et Cie, Paris, France) V.9-15, 1914-77. Volume(issue)/page/year: 7,537,1962

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
1544

[ WGK Germany ]:
3

[ RTECS ]:
YM3875000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933990090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Tropine dehydrogenase: purification, some properties and an evaluation of its role in the bacterial metabolism of tropine.

Biochem. J. 307 ( Pt 2) , 603-8, (1995)

Tropine dehydrogenase was induced by growth of Pseudomonas AT3 on atropine, tropine or tropinone. It was NADP(+)-dependent and gave no activity with NAD+. The enzyme was very unstable but a rapid puri...

The metabolism of atropine in man.

J. Pharm. Pharmacol. 38(10) , 781-4, (1986)

A metabolic pattern of atropine in man, based on the detection of radiolabelled products in urine by high performance liquid chromatography after administration of [3H]atropine sulphate to a normal vo...

Determination of nitrogen-15 isotope fractionation in tropine: evaluation of extraction protocols for isotope ratio measurement by isotope ratio mass spectrometry.

Rapid Commun. Mass Spectrom. 23(24) , 4031-7, (2009)

N-Demethylation of tropine is an important step in the degradation of this compound and related metabolites. With the purpose of understanding the reaction mechanism(s) involved, it is desirable to me...


More Articles


Related Compounds