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Tropine benzilate

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From Wikipedia, the free encyclopedia

Anticholinergic

Pharmaceutical compound

Tropine benzilate
Clinical data

Other names	Tropine benzylate, BAT, TB, #9447, BETE, BTE, Glykin, Glypin
Identifiers
IUPAC name endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-2,2-diphenylacetate
CAS Number	3736-36-5 stereochem unspec: 42487-29-6 HCl salt: 1674-94-8 74051-39-1
PubChemCID	1138166
ChemSpider	16736072
UNII	3M2OLH58KE
ChEMBL	ChEMBL1906907
CompTox Dashboard(EPA)	DTXSID70958468
ECHA InfoCard	100.125.953
Chemical and physical data
Formula	C₂₂H₂₅NO₃
Molar mass	351.446 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O
InChI InChI=1S/C22H25NO3/c1-23-18-12-13-19(23)15-20(14-18)26-21(24)22(25,16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-20,25H,12-15H2,1H3/t18-,19+,20? Key:XXVZGWNHSCGMCT-YOFSQIOKSA-N

Tropine benzilate also known asglipin is an ester formed betweentropine andbenzilic acid.^[1] Like its structural relatives such as atropine and scopolamine, tropine benzilate is considered amuscarinic antagonist, meaning it binds to and blocksmuscarinic acetylcholine receptors in the nervous system and various tissues.

The substance was first described in 1936 and was shown to relaxsmooth muscle and block signals from thevagus nerve.^[2] It was also later shown to block stomach acid secretion in dogs.^[3]

It is a chemicaldeliriant similar to two related substances, namely3-quinuclidinyl benzilate andCS-27349.Atropine is also based on tropine alkaloid but differs in the structure in that it containstropic acid and notbenzilic acid for the aromatic portion of the ester moiety. Tropine benzilate is less commonly sold as a tertiary amine, but is usually encountered as the quaternary amineFlutropium bromide.

Synthesis

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Tropine benzilate may be synthesized by reacting tropine with methyl benzilate in atransesterification reaction.^[4]

References

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^Hromatka O, Csoklich C, Hofbauer I (November 1952). "Über den Tropin-benzilsäureester".Monatshefte für Chemie und verwandte Teile anderer Wissenschaften.83 (6):1321–1325.doi:10.1007/BF00913835.
^Kreitmair H (1936). "The pharmacological properties of the benzilic acid ester of tropin".Klinische Wochenschrift.15:676–678.doi:10.1007/BF01778785.ISSN 0023-2173.
^Utepbergenova RK (1966). "Effect of a new cholinolytic glypine [diphenylglycolic acid tropine ester] on the secretory function of the stomach".Trudy Instituta Eksperimental'noi Meditsiny Akademii Meditsinskikh Nauk SSSR (in Russian).9 (3):28–30.ISSN 0515-9261.
^Example 4 inUS 20080027094, Nakai H, Nishiyama T, Nakamura N, Fujita M, "Tropane Compounds and Pharmaceutical Compositions Comprising the Same as an Active Ingredient", published 31 January 2008, assigned to Ono Pharmaceutical Co., Ltd.