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Alfentanil

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Also known as: 69049-06-5, Alfenta, Rapifen, Alfentanil hcl, R 39209, Alfentanil hydrochloride [usan]

Molecular Formula

C₂₁H₃₃ClN₆O₃

Molecular Weight

453.0 g/mol

InChI Key

AQORHZJDCHLLJN-UHFFFAOYSA-N

FDA UNII

333JTI7A2M

A short-acting opioid anesthetic and analgesic derivative of FENTANYL. It produces an early peak analgesic effect and fast recovery of consciousness. Alfentanil is effective as an anesthetic during surgery, for supplementation of analgesia during surgical procedures, and as an analgesic for critically ill patients.

1 2D Structure

Alfentanil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide;hydrochloride

2.1.2 InChI

InChI=1S/C21H32N6O3.ClH/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26;/h6-10H,4-5,11-17H2,1-3H3;1H

2.1.3 InChI Key

AQORHZJDCHLLJN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCN3C(=O)N(N=N3)CC)COC.Cl

2.2 Other Identifiers

2.2.1 UNII

333JTI7A2M

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alfenta

2. Alfentanil

3. Alfentanyl

4. Fanaxal

5. Limifen

6. R 39209

7. R-39209

8. R39209

9. Rapifen

2.3.2 Depositor-Supplied Synonyms

1. 69049-06-5

2. Alfenta

3. Rapifen

4. Alfentanil Hcl

5. R 39209

6. Alfentanil Hydrochloride [usan]

7. 333jti7a2m

8. R-39209

9. Mls002320667

10. Ncgc00247354-02

11. N-[1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl]-n-phenylpropanamide;hydrochloride

12. Smr001338813

13. Einecs 273-846-3

14. Unii-333jti7a2m

15. Fentalim

16. R-39,209

17. Ox-51

18. Alfentanil Hydrochloride Cii

19. Dsstox_cid_28853

20. Dsstox_rid_83122

21. Dsstox_gsid_48927

22. Schembl40459

23. Alfentanil Hydrochloride Solution

24. Chembl1200531

25. Dtxsid0048927

26. Alfentanil Hydrochloride Anhydrous

27. Tox21_112878

28. Alfentanil Hydrochloride [mi]

29. Akos015966535

30. Sb17330

31. Alfentanil Hydrochloride [who-dd]

32. Anhydrous Alfentanil Hydrochloride

33. N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-4-(methoxymethyl)piperidin-4-yl)-n-phenylpropionamide Hydrochloride

34. Propanamide, N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-4-(methoxymethyl)-4-piperidinyl)-n-phenyl-, Monohydrochloride

35. Cas-69049-06-5

36. Db-055216

37. Anhydrous Alfentanil Hydrochloride [mart.]

38. Q27256225

39. Alfentanil Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

40. N-(1-(2-(4-ethyl-5-oxo-2-tetrazolin-1-yl)-ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Monohydrochloride

41. Propanamide, N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-4-(methoxymethyl)-4-piperidinyl)-n-phenyl, Monohydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₃ClN₆O₃
Molecular Weight	453.0 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	452.2302666 g/mol
Monoisotopic Mass	452.2302666 g/mol
Topological Polar Surface Area	81 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	614
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

Narcotics

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)

Analgesics, Opioid

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

Anesthetics, Intravenous

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)

4.2 FDA Pharmacological Classification

4.2.1 Pharmacological Classes

Opioid Agonist [EPC]; Full Opioid Agonists [MoA]