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378704

Sigma-Aldrich

Tropane

98%

Synonym(s):

8-Methyl-8-azabicyclo[3.2.1]octane

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About This Item

Empirical Formula (Hill Notation):
C8H15N
CAS Number:
Molecular Weight:
125.21
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
Assay:
98%

Assay

98%

form

liquid

refractive index

n20/D 1.477 (lit.)

bp

167-169 °C (lit.)

density

0.931 g/mL at 25 °C (lit.)

SMILES string

CN1[C@H]2CCC[C@@H]1CC2

InChI

1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+

InChI key

XLRPYZSEQKXZAA-OCAPTIKFSA-N

General description

Tropane (8-methyl-8-azabicyclo[3.2.1]-octane) is a bridged bicyclic N-containing compound.[1] The 8-methyl-8-azabicyclo[3.2.1]-octane has a tropane ring system, which is an important substructure in a number of natural products and synthetic compounds of biological and medicinal importance.[2] Production of tropane alkaloid in callus and root cultures of seven Hyoscyamus species has been studied.[3] Tropane derivatives are reported to undergo rapid N-methyl inversion.[4]

Pictograms

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Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

107.6 °F - closed cup

Flash Point(C)

42 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A Kokotkiewicz et al.
Food chemistry, 221, 535-540 (2016-12-17)
Thin layer chromatographic methods for quantitative determination of nightshade-specific tropane (l-hyoscyamine, scopolamine) and steroidal alkaloids (α-solanine, α-chaconine) in goji berries (L. barbarum L., Solanaceae) were developed. The analysis of tropane derivatives included separation on silica gel-coated HPTLC plates using mobile
Enhancing Tropane Alkaloid Production Based on the Functional Identification of Tropine-Forming Reductase in
Kaihui Zhao et al.
Frontiers in plant science, 8, 1745-1745 (2017-11-01)
An improved synthesis of (+)-2-tropinone.
Zhang C, et al.
The Journal of Organic Chemistry, 62(22), 7888-7889 (1997)
Abigail Moreno-Pedraza et al.
Metabolites, 9(7) (2019-07-07)
different Solanaceae and Erythroxylaceae species produce tropane alkaloids. These alkaloids are the starting material in the production of different pharmaceuticals. The commercial demand for tropane alkaloids is covered by extracting them from cultivated plants. Datura stramonium is cultivated under greenhouse
Tehetena Mesganaw et al.
Organic process research & development, 18(9), 1097-1104 (2014-10-08)
A Rh-catalyzed C-H bond activation/alkenylation/electrocyclization cascade reaction provides diverse 1,2-dihydropyridines from simple and readily available precursors. The reaction can be carried out at low (<1%) Rh-catalyst loadings, and the use of the robust, air-stable Rh precatalyst, [RhCl(cod)]

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