Tropine benzilate

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;
PubChem CID	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 as glipin is an ester formed between tropine and benzilic acid.^[1] Like its structural relatives such as atropine and scopolamine, tropine benzilate is considered a muscarinic antagonist, meaning it binds to and blocks muscarinic acetylcholine receptors in the nervous system and various tissues.

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

It is a chemical deliriant similar to two related substances, namely 3-quinuclidinyl benzilate and CS-27349. Atropine is also based on tropine alkaloid but differs in the structure in that it contains tropic acid and not benzilic 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 amine Flutropium bromide.

Synthesis

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

References

^ Hromatka O, Csoklich C, Hofbauer I (November 1952). "Über den Tropin-benzilsäureester". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften. 83: 1321–1325. doi:10.1007/BF00913835.
^ Kreitmair H (1936). "The pharmacological properties of the benzilic acid ester of tropin". Klinische Wochenschrift. 15: 676–678. 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 in US 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.

[Hromatka-1] Hromatka O, Csoklich C, Hofbauer I (November 1952). "Über den Tropin-benzilsäureester". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften. 83: 1321–1325. doi:10.1007/BF00913835.

[2] Kreitmair H (1936). "The pharmacological properties of the benzilic acid ester of tropin". Klinische Wochenschrift. 15: 676–678. ISSN 0023-2173.

[3] 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.

[4] Example 4 in US 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.

[1]

[2]

[3]

[4]