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Chemistry

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Also known as: 14198-59-5, Mls000028478, Cephaeline methyl ether hydrochloride, Emetine (hydrochloride), Smr000058444, (2s,3r,11bs)-2-[[(1r)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizine;hydrochloride

Molecular Formula

C₂₉H₄₁ClN₂O₄

Molecular Weight

517.1 g/mol

InChI Key

HUEYSSLYFJVUIS-MRFSYGAJSA-N

The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.

1 2D Structure

Emetine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine;hydrochloride

2.1.2 InChI

InChI=1S/C29H40N2O4.ClH/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24;/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3;1H/t18-,21-,24+,25-;/m0./s1

2.1.3 InChI Key

HUEYSSLYFJVUIS-MRFSYGAJSA-N

2.1.4 Canonical SMILES

CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC.Cl

2.1.5 Isomeric SMILES

CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC.Cl

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Dihydrochloride, Emetine

2. Emetine

3. Emetine Dihydrochloride

4. Hydrochloride, Emetine

5. Ipecine

6. Methylcephaeline

2.2.2 Depositor-Supplied Synonyms

1. 14198-59-5

2. Mls000028478

3. Cephaeline Methyl Ether Hydrochloride

4. Emetine (hydrochloride)

5. Smr000058444

6. (2s,3r,11bs)-2-[[(1r)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizine;hydrochloride

7. Nsc33669

8. Nsc-33669

9. Emetinal

10. Erketin

11. Encol

12. Emetinehydrochloride

13. Emetine, Hydrochloride

14. Emetine Monohydrochloride

15. Opera_id_1460

16. Cephaeline Methyl Ether Hcl

17. Schembl636599

18. Chembl513000

19. Niosh/jy5800000

20. Hy-b1479c

21. Dtxsid80424947

22. Nsc752340

23. S3233

24. Akos024374935

25. Nsc-752340

26. Cs-0103259

27. Jy58000000

28. Emetan,7',10,11-tetramethoxy-, Dihydrochloride

29. Q-100155

30. 2h-benzo[a]quinolizine,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[(1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl]-, Dihydrochloride

2.3 Create Date

2006-05-25

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₄₁ClN₂O₄
Molecular Weight	517.1 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	516.2754855 g/mol
Monoisotopic Mass	516.2754855 g/mol
Topological Polar Surface Area	52.2 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	679
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Amebicides

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)

Antinematodal Agents

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

Cathartics

Agents that are used to stimulate evacuation of the bowels. (See all compounds classified as Cathartics.)

Emetics

Agents that cause vomiting. They may act directly on the gastrointestinal tract, bringing about emesis through local irritant effects, or indirectly, through their effects on the chemoreceptor trigger zone in the postremal area near the medulla. (See all compounds classified as Emetics.)

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

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