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Wikipedia

Tropine

Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol.[4] It is a poisonous white hygroscopic crystalline powder.[3] It is a heterocyclic alcohol and an amine.[3]

Tropine
Names
Preferred IUPAC name
(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Other names
α-Tropine; Tropanol
Identifiers
  • 120-29-6 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10180559 N
ECHA InfoCard 100.003.986
MeSH Tropine
  • 8424
UNII
  • 7YXR19M72Y Y
  • DTXSID2049399
  • InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ N
    Key: CYHOMWAPJJPNMW-JIGDXULJSA-N N
  • InChI=1/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+
    Key: CYHOMWAPJJPNMW-JIGDXULJBD
  • CN1[C@@H]2CC[C@H]1C[C@H](C2)O
Properties
C8H15NO
Molar mass 141.214 g·mol−1
Appearance White hygroscopic crystalline powder[1][2][3] or plates
Odor Amine-like[2]
Density 1.045 g/cm3 at 25 °C[2]
1.016 g/cm3 at 100 °C
Melting point 64 °C (147 °F; 337 K)
Boiling point 233 °C (451 °F; 506 K)
Solubility Very soluble in water, diethyl ether, ethanol[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
GHS labelling:
Danger
H301, H302, H312, H332
P261, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P405, P501
Lethal dose or concentration (LD, LC):
  • >2000 mg/kg (rat, oral)[2]
  • 139 mg/kg (mouse, intraperitoneal)
  • >50 mg/kg (rabbit, intravenous)
  • 280 mg/kg (mouse, intraperitoneal)
  • >50 mg/kg (rabbit, intravenous)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Tropine is a central building block of many chemicals active in the nervous system, including tropane alkaloids. Some of these compounds, such as long-acting muscarinic antagonists are used as medicines because of these effects.[5]

Occurrence edit

Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium).[1]

Chemistry edit

Synthesis edit

It can be prepared by hydrolysis of atropine[6] or other solanaceous alkaloids.[3]

See also edit

References edit

  1. ^ a b c https://pubchem.ncbi.nlm.nih.gov/compound/8424
  2. ^ a b c d https://www.sigmaaldrich.com/GB/en/sds/aldrich/93550
  3. ^ a b c d https://www.merriam-webster.com/medical/tropine
  4. ^ a b Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–564, ISBN 0-8493-0594-2
  5. ^ Ping, Yu; Li, Xiaodong; You, Wenjing; Li, Guoqiang; Yang, Mengquan; Wei, Wenping; Zhou, Zhihua; Xiao, Youli (10 June 2019). "Production of the Plant-Derived Tropine and Pseudotropine in Yeast". ACS Synthetic Biology. 8 (6): 1257–1262. doi:10.1021/acssynbio.9b00152. PMID 31181154. S2CID 184484993.
  6. ^ "Cocaine analog in two steps from native plant material".


tropine, derivative, tropane, containing, hydroxyl, group, third, carbon, also, called, tropanol, poisonous, white, hygroscopic, crystalline, powder, heterocyclic, alcohol, amine, namespreferred, iupac, name, methyl, azabicyclo, octan, olother, names, tropanol. Tropine is a derivative of tropane containing a hydroxyl group at the third carbon It is also called 3 tropanol 4 It is a poisonous white hygroscopic crystalline powder 3 It is a heterocyclic alcohol and an amine 3 Tropine NamesPreferred IUPAC name 1R 3r 5S 8 Methyl 8 azabicyclo 3 2 1 octan 3 olOther names a Tropine TropanolIdentifiersCAS Number 120 29 6 Y3D model JSmol Interactive imageChemSpider 10180559 NECHA InfoCard 100 003 986MeSH TropinePubChem CID 8424UNII 7YXR19M72Y YCompTox Dashboard EPA DTXSID2049399InChI InChI 1S C8H15NO c1 9 6 2 3 7 9 5 8 10 4 6 h6 8 10H 2 5H2 1H3 t6 7 8 NKey CYHOMWAPJJPNMW JIGDXULJSA N NInChI 1 C8H15NO c1 9 6 2 3 7 9 5 8 10 4 6 h6 8 10H 2 5H2 1H3 t6 7 8 Key CYHOMWAPJJPNMW JIGDXULJBDSMILES CN1 C H 2CC C H 1C C H C2 OPropertiesChemical formula C 8H 15N OMolar mass 141 214 g mol 1Appearance White hygroscopic crystalline powder 1 2 3 or platesOdor Amine like 2 Density 1 045 g cm3 at 25 C 2 1 016 g cm3 at 100 CMelting point 64 C 147 F 337 K Boiling point 233 C 451 F 506 K Solubility Very soluble in water diethyl ether ethanol 4 HazardsOccupational safety and health OHS OSH Main hazards ToxicGHS labelling PictogramsSignal word DangerHazard statements H301 H302 H312 H332Precautionary statements P261 P264 P270 P271 P280 P301 P316 P301 P317 P302 P352 P304 P340 P317 P321 P330 P362 P364 P405 P501Lethal dose or concentration LD LC LD50 median dose gt 2000 mg kg rat oral 2 139 mg kg mouse intraperitoneal gt 50 mg kg rabbit intravenous 280 mg kg mouse intraperitoneal gt 50 mg kg rabbit intravenous 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Tropine is a central building block of many chemicals active in the nervous system including tropane alkaloids Some of these compounds such as long acting muscarinic antagonists are used as medicines because of these effects 5 Contents 1 Occurrence 2 Chemistry 2 1 Synthesis 3 See also 4 ReferencesOccurrence editTropine is a natural product found in the plants of deadly nightshade Atropa belladonna and devil s trumpet Datura stramonium 1 Chemistry editSynthesis edit It can be prepared by hydrolysis of atropine 6 or other solanaceous alkaloids 3 See also editPseudotropine Atropine Tropinone Tropane alkaloidReferences edit a b c https pubchem ncbi nlm nih gov compound 8424 a b c d https www sigmaaldrich com GB en sds aldrich 93550 a b c d https www merriam webster com medical tropine a b Lide David R 1998 Handbook of Chemistry and Physics 87 ed Boca Raton Florida CRC Press pp 3 564 ISBN 0 8493 0594 2 Ping Yu Li Xiaodong You Wenjing Li Guoqiang Yang Mengquan Wei Wenping Zhou Zhihua Xiao Youli 10 June 2019 Production of the Plant Derived Tropine and Pseudotropine in Yeast ACS Synthetic Biology 8 6 1257 1262 doi 10 1021 acssynbio 9b00152 PMID 31181154 S2CID 184484993 Cocaine analog in two steps from native plant material nbsp This article about a heterocyclic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Tropine amp oldid 1143232088, wikipedia, wiki, book, books, library,

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