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Chemistry

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Also known as: Pentyl nitrite, 463-04-7, N-amyl nitrite, N-pentyl nitrite, Nitrous acid, pentyl ester, Pentyl alcohol, nitrite
Molecular Formula
C5H11NO2
Molecular Weight
117.15  g/mol
InChI Key
CSDTZUBPSYWZDX-UHFFFAOYSA-N
FDA UNII
H2HUX79FYK

Amyl Nitrite
A vasodilator that is administered by inhalation. It is also used recreationally due to its supposed ability to induce euphoria and act as an aphrodisiac.
1 2D Structure

Amyl Nitrite

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pentyl nitrite
2.1.2 InChI
InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3
2.1.3 InChI Key
CSDTZUBPSYWZDX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCON=O
2.2 Other Identifiers
2.2.1 UNII
H2HUX79FYK
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Nitrite, Amyl

2.3.2 Depositor-Supplied Synonyms

1. Pentyl Nitrite

2. 463-04-7

3. N-amyl Nitrite

4. N-pentyl Nitrite

5. Nitrous Acid, Pentyl Ester

6. Pentyl Alcohol, Nitrite

7. Nitrous Acid Pentyl Ester

8. H2hux79fyk

9. Chebi:55344

10. Pentylnitrite

11. Ccris 763

12. Einecs 207-332-7

13. Unii-h2hux79fyk

14. Brn 1701241

15. N-pentylnitrite

16. Ai3-25184

17. Amyl 1 Nitrite

18. 1-pentyl Nitrite

19. N-phenyl Nitrile

20. Nitrite De Pentyle

21. Dsstox_cid_4522

22. Un 1113 (related)

23. Pentyl Nitrite, Aldrichcpr

24. Dsstox_rid_77442

25. Dsstox_gsid_24522

26. Schembl34065

27. 4-01-00-01644 (beilstein Handbook Reference)

28. Chembl3188202

29. Dtxsid3024522

30. Hsdb 8468

31. Amy3989

32. Tox21_202898

33. Mfcd00036132

34. Stl268844

35. Zinc20230701

36. Akos015853631

37. Db01612

38. Ncgc00260444-01

39. Cas-463-04-7

40. Ls-13085

41. A0455

42. Ft-0622367

43. A19477

44. D88264

45. A802198

46. Q412350

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 117.15 g/mol
Molecular Formula C5H11NO2
XLogP31.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass117.078978594 g/mol
Monoisotopic Mass117.078978594 g/mol
Topological Polar Surface Area38.7 Ų
Heavy Atom Count8
Formal Charge0
Complexity56.4
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ Presented is a case of idiopathic priapism that was successfully treated with inhalation of amyl nitrite. Routine treatment measures had failed. The same patient presented on several other occasions in a similar fashion. Each time amyl nitrite was successful. An investigation for diseases known to be associated with priapism proved negative. Due to the frequency of recurrences, definitive surgical management was offered. The patient refused and has been lost to follow up.

PMID:6132570 Parrillo SJ, Manfrey S; Ann Emerg Med 12 (4): 226-7 (1983)


/EXPL THER/ Acute catastrophic pulmonary vasoconstriction frequently leads to cardiovascular collapse. Rapid and selective pulmonary vasodilation is desired in order to restore hemodynamic stability. This pilot study examined the effectiveness of inhaled amyl nitrite as a selective pulmonary vasodilator. Nine adult swine were anesthetized. Acute pulmonary hypertension with hemodynamic collapse was induced with a bolus administration of a thromboxane analogue, U46619. Six animals then received a capsule of amyl nitrite. The administration of inhaled amyl nitrite decreased mean pulmonary artery pressure from 42 +/- 3 to 22 +/ 3 mm Hg at five minutes (p < 0.05), with a concomitant increase in cardiac output and mean arterial pressure. Pulmonary vascular resistance decreased from 4889 +/- 1338 to 380 +/- 195 dyne. sec. cm(-5) (by 92% from the maximal pulmonary hypertension change), with significant improvement in systemic hemodynamics. During acute thromboxane-mediated pulmonary hypertension with cardiovascular collapse, prompt administration of inhaled amyl nitrite was effective in restoring pulmonary and systemic hemodynamics within five minutes.

PMID:17644883 Muehlschlegel JD et al; Ann Card Anaesth 10 (2): 113-20 (2007)


/EXPL THER/ Amyl nitrite is a smooth muscle relaxant that has been used clinically to facilitate uterine relaxation in difficult deliveries. In this retrospective study, we evaluate the safety of amyl nitrite use during preterm cesarean deliveries, and we assess possible advantageous effects on surgical incision choice. Women who received amyl nitrite cesarean section were compared to a control group matched for gestational age, fetal presentation, and mode of delivery who did not receive amyl nitrite. There were no statistical differences between the groups in the independent variables (maternal age, parity, medical or obstetric history, type of anesthesia, anesthesia or obstetric attending physician, antepartum hematocrit, or neonatal weight). Outcome (dependent) variables (estimated blood loss, Apgar scores, postpartum hematocrit, cord gases, or postpartum complications) were assessed, and there were no significant differences between the groups. Low transverse cesarean section was performed more frequently in the amyl nitrite group (58 of 64) than in the comparison group (48 of 64) (p less than 0.03). Considering the 128 women with and without amyl nitrite together, the decrease in hematocrit observed postpartum was greater after classic section (7%) than after low transverse section (4%) (p less than 0.002). We conclude that the use of amyl nitrite during preterm cesarean section poses no threat to mother or fetus and may facilitate delivery by allowing the performance of a low transverse rather than a classic cesarean section without maternal or neonatal complications.

PMID:1352684 Hendricks SK et al; Am J Perinatol 9 (4): 289-92 (1992)


4.2 Drug Indication

For the rapid relief of angina pectoris.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Amyl nitrite, in common with other alkyl nitrites, is a potent vasodilator. It expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrite functions as a source of nitric oxide, which signals for relaxation of the involuntary muscles. Adverse effects are related to this pharmacological activity and include hypotension, headache, flushing of the face, tachycardia, dizziness, and relaxation of involuntary muscles, especially the blood vessel walls and the anal sphincter.


5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


5.3 ATC Code

V - Various

V03 - All other therapeutic products

V03A - All other therapeutic products

V03AB - Antidotes

V03AB22 - Amyl nitrite


5.4 Absorption, Distribution and Excretion

Absorption

Amyl nitrite vapors are absorbed rapidly through the pulmonary alveoli, manifesting therapeutic effects within one minute after inhalation.


5.5 Metabolism/Metabolites

Hepatic. The drug is metabolized rapidly, probably by hydrolytic denitration; approximately one-third of the inhaled amyl nitrite is excreted in the urine.


5.6 Mechanism of Action

Amyl nitrite's antianginal action is thought to be the result of a reduction in systemic and pulmonary arterial pressure (afterload) and decreased cardiac output because of peripheral vasodilation, rather than coronary artery dilation. Amyl nitrite is a source of nitric oxide, which accounts for the mechanism described above. As an antidote (to cyanide poisoning), amyl nitrite promotes formation of methemoglobin, which combines with cyanide to form nontoxic cyanmethemoglobin.


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23-Nov-2021
08-Aug-2024
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