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Terpin

Synopsis, Chemistry

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Also known as: 2451-01-6, Terpin monohydrate, Terpin (hydrate), P-menthane-1,8-diol monohydrate, Terpin cis-form hydrate, Cis-terpin hydrate

Molecular Formula

C₁₀H₂₂O₃

Molecular Weight

190.28 g/mol

InChI Key

JGKJMBOJWVAMIJ-UHFFFAOYSA-N

FDA UNII

S3V868548T

Terpin hydrate is an expectorant, commonly used to loosen mucus and ease congestion in patients presenting with acute or chronic bronchitis, and related pulmonary conditions. It is derived from sources such as turpentine, oregano, thyme and eucalyptus. It was popular in the United States since the late nineteenth century, but was removed from marketed medications in the 1990s after FDA stated that "based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients". Elixirs of terpin hydrate are still available to patients as prescription medications to be prepared by specialty compounding pharmacies.

1 2D Structure

Terpin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol;hydrate

2.1.2 InChI

InChI=1S/C10H20O2.H2O/c1-9(2,11)8-4-6-10(3,12)7-5-8;/h8,11-12H,4-7H2,1-3H3;1H2

2.1.3 InChI Key

JGKJMBOJWVAMIJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1(CCC(CC1)C(C)(C)O)O.O

2.2 Other Identifiers

2.2.1 UNII

S3V868548T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(2'-hydroxypropan-2'-yl)-5-methylcyclohexanol

2. 2-hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol

3. Geranodyle

4. P-menthane-1,8-diol

5. P-menthane-3,8-diol

6. Para-menthane-3,8-diol

7. Terpin

8. Terpin, Monohydrate(cis)-isomer

9. Terpin, Titanium (+4) Salt

2.3.2 Depositor-Supplied Synonyms

1. 2451-01-6

2. Terpin Monohydrate

3. Terpin (hydrate)

4. P-menthane-1,8-diol Monohydrate

5. Terpin Cis-form Hydrate

6. Cis-terpin Hydrate

7. Terpinol Hydrate

8. Terpinene Hydrate

9. 4-(2-hydroxypropan-2-yl)-1-methylcyclohexanol Hydrate

10. Cyclohexanemethanol, 4-hydroxy-alpha,alpha,4-trimethyl-, Monohydrate

11. Cis-p-methane-1,8-diol Monohydrate

12. Terpinol

13. Cis-p-menthane-1,8-diol Monohydrate

14. Terpin Monohydrate;cis-terpin Hydrate

15. Nsc-760418

16. S3v868548t

17. Terpin Hydrate (usp)

18. Terpin Hydrate [usp]

19. Terpine Hydrate

20. Terpinhydrate

21. Ai3-01762

22. Schembl29867

23. Terpin Hydrate [vandf]

24. Schembl2487459

25. Terpin Hydrate [mart.]

26. Chembl2105614

27. Terpin Hydrate [usp-rs]

28. Terpin Hydrate [who-dd]

29. Unii-s3v868548t

30. 4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol Hydrate

31. 4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol,hydrate

32. Dtxsid00947401

33. Hms3264b12

34. P-menthane-1,8-diol, Monohydrate

35. Hy-b1063

36. Mfcd00167312

37. S4577

38. Terpin Cis-form Hydrate [mi]

39. Akos016013500

40. Akos024288517

41. Terpin Hydrate [usp Monograph]

42. Ccg-213672

43. Ccg-266507

44. Cs-4619

45. Db13163

46. Ks-1430

47. Nsc 760418

48. Terpin Monohydrate [ep Monograph]

49. D06081

50. D92597

51. Sr-01000944230

52. J-015549

53. Q2273017

54. Sr-01000944230-1

55. 4-(2-hydroxypropan-2-yl)-1-methyl-cyclohexan-1-ol

56. 4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol;hydrate

57. 4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol--water (1/1)

58. Rel-(1s,4s)-4-(2-hydroxypropan-2-yl)-1-methylcyclohexanol Hydrate

59. Terpin Hydrate, United States Pharmacopeia (usp) Reference Standard

60. Cis-4-hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol Monohydrate

61. Cyclohexanemethanol, 4-hydroxy-.alpha.,.alpha.,4-trimethyl-, Hydrate (1:1), Cis-

62. Cyclohexanemethanol, 4-hydroxy-.alpha.,.alpha.,4-trimethyl-, Monohydrate

63. Cyclohexanemethanol, 4-hydroxy-alpha,alpha,4-trimethyl-, Hydrate (1:1), Cis-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₂O₃
Molecular Weight	190.28 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	190.15689456 g/mol
Monoisotopic Mass	190.15689456 g/mol
Topological Polar Surface Area	41.5 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	155
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 Drug and Medication Information

4.1 Drug Indication

Terpin hydrate is used in the treatment of acute and chronic bronchitis, pneumonia, bronchiectasis, chronic obstructive pulmonary disease, infectious and inflammatory diseases of the upper respiratory tract.

5 Pharmacology and Biochemistry

5.1 Pharmacology

It acts to facilitate the removal of mucus from the respiratory tract. It prevents the exacerbation of excessive mucus production and secretion due to airway bacterial or viral infections, asthma or chronic bronchitis. Expectorants like terpin hydrate change mucus consistency and make coughing more productive.

5.2 MeSH Pharmacological Classification

Expectorants

Agents that increase mucous excretion. Mucolytic agents, that is drugs that liquefy mucous secretions, are also included here. (See all compounds classified as Expectorants.)

5.3 Mechanism of Action

Terpin hydrate improves mucociliary function by working directly on the bronchial secretory cells in the lower respiratory tract to liquify and facilitate the elimination of bronchial secretionsas well as exerting a weak antiseptic effect on the pulmonary parenchyma. It is thought to increase the amount of fluid in the respiratory tract, which increases the flow and clearance of local irritants and as well as reducing the viscosity of mucus.