Slide share of atropine

Atropine discussed in detail

1. Central University of Kashmir Department of zoology Name : Mushtaq Ahmad Khan Enrollment No: 1915cukmr23 Semester. : 6th Topic. : Atropine Date of submission:1 st July 2022 Submitted to. : Dr. Skindar SiR

2. ATROPINE

3. It is a Solanaceous alkaloid . Molecular Formula:C17H23NO3 Melting Point :118°C It occurs in Atropa belladonna along with Hyoscyamine . Hyoscyamine is optically active ( levorotatory ) but readily recimises to atropine when warmed with ethanolic alkaline solution. Thus atropine is (+/-) hyoscyamine. Atropine on reaction with Barium Hydroxide gives plus minus tropic acid and plus tropine.

4. Tropic acid Molecular Formula. C9O3H10 Melting point 117°C It is a saturated compound Usual tests Show that it contains one carboxyl group and one alcoholic group. When heated strongly,It loses a molecule of water and forms atropic acid and atropic acid on oxidation gives benzoic acid. This Shows that tropic acid and atropic acid contains benzene ring with one side chain.

5. 1 st is cinnamic acid. 2 nd must be atropic acid as addition of water molecule to this gives tropic acid. Two structures are possible for tropic acid.

6. Tropic acid has been shown to be 4 th by synthesis from acetophenone by Mackenzie and Wood.

7. 3 rd is atrolactic acid and it’s dehydration to 2 nd confirms the structure of atropic acid . It should be noted that addition of HCl takes place contrary to markownikoff`s rule . Blicke et al have also synthesized the tropic acid by boiling phenylacetic acid with isopropylmagnesium chloride in etheral solution and then treating the product with formaldehyde.

8. Tropine Also called Tropanol. Molecular Formula:.. C Melting point 63°C. Behaves as saturated compound with one alcoholic group. Structure was investigated by Ladenberg who showed molecule contains reduced pyridine nucleus.

9. The formation of methyl chloride indicates presence of N-methyl group. Isolation of 2-ethylpyridine shows the presence of this nucleus . On this evidance Ladenberg proposed the following structures.

10. Merling by oxidation of tropine with cromium trioxide obtained plus minus tropic acid. Tropic acid is a dicarboxylic acid. There is no loss of carbon in its formation ,the hydroxyl group in tropine must therefore be in a ring system. Thus Ladenburg formula is untainable. Merling proposed the following structures

11. Willstatter examined the oxidation products of tropine obtained as follows . Tropinone behaved as a ketone . Willstatter also showed that tropinone forms dibenzalidine derivative with benzeldehyde and di-oximino derivative with amylnitrite and Hydrochloric acid. Thus tropinone contains CHCOCH groups and it follows that Merling formula is untainable. Willstatter proposed the following structure of tropinone. This structure fit the facts best and was supported by evidences.

12. The structure of tropine has been confirmed by synthesis,one by Willstatter and other by Robinson. Robinson synthesis. When mixture of succinaldehyde,methylamine and acetone is allowed for 30 minutes, tropinone is produced

13. +

14. Refrence. Jonathan Clayden ( University of Manchester ) Nick Greeves (University of Liverpool) Stuart Warren (University of Cambridge) Organic chemistry Volume II by I.L .Finar

15. Thank you