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2D Structure
Also known as: Trimethylene, 75-19-4, Ciclopropano, Cyclopropanum, Zyklopropan, Trimethylene (cyclic)
Molecular Formula
C3H6
Molecular Weight
42.08  g/mol
InChI Key
LVZWSLJZHVFIQJ-UHFFFAOYSA-N
FDA UNII
99TB643425

Cyclopropane was initially investigated because it was thought to be the toxic element in ethylene. Instead, it turned out to be an excellent anesthetic with very rapid onset and recovery while maintaining stable hemodynamics. Its use was ultimately limited because it was highly explosive.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
cyclopropane
2.1.2 InChI
InChI=1S/C3H6/c1-2-3-1/h1-3H2
2.1.3 InChI Key
LVZWSLJZHVFIQJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CC1
2.2 Other Identifiers
2.2.1 UNII
99TB643425
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Trimethylene

2.3.2 Depositor-Supplied Synonyms

1. Trimethylene

2. 75-19-4

3. Ciclopropano

4. Cyclopropanum

5. Zyklopropan

6. Trimethylene (cyclic)

7. Cyclopropan

8. Chebi:30365

9. 99tb643425

10. Cyclopropane [inn]

11. Cyclopropanum [inn-latin]

12. Ciclopropano [inn-spanish]

13. Hsdb 812

14. Cyclopropane [usp:inn]

15. Einecs 200-847-8

16. Rc 270

17. Un1027

18. Cyclopropnane

19. Unii-99tb643425

20. Cyclopropane [anaesthetics, Volatile]

21. Cyclopropane, >=99%

22. Cyclopropane (usp/inn)

23. Cyclopropane [mi]

24. Cyclopropane [hsdb]

25. Cyclopropane [mart.]

26. Cyclopropane [who-dd]

27. Chembl1796999

28. Dtxsid4058786

29. Cyclopropane [usp Impurity]

30. Mfcd00001268

31. Akos015915611

32. Db13984

33. Un 1027

34. Cyclopropane [un1027] [flammable Gas]

35. D03627

36. Q80250

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 42.08 g/mol
Molecular Formula C3H6
XLogP31.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass42.0469501914 g/mol
Monoisotopic Mass42.0469501914 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count3
Formal Charge0
Complexity4.8
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

Anesthetics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


/FORMER USE:/WITH CYCLOPROPANE, THE MARGIN OF SAFETY IS FAIRLY WIDE, 13% TO 20% PRODUCING ANESTHESIA AND 40% RESPIRATORY ARREST.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 54


/FORMER USE:/ IT IS THE MOST POTENT OF THE ANESTHETIC GASES, BEING APPROX FIVE TIMES AS POTENT AS ETHYLENE & SEVEN TIMES AS POTENT AS NITROUS OXIDE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 980


/FORMER USE:/ MEDICATION (VET): INHALATION ANESTHETIC

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 464


4.2 Drug Warning

SECOND GAS EFFECT. ...INCREASED INSPIRATORY VOL CARRIES WITH IT ANY OTHER GAS GIVEN CONCOMITANTLY AND HENCE WILL ACCELERATE THE RISE OF ALVEOLAR CONCN OF SECOND GAS.

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 113


CYCLOPROPANE CAUSES NEONATAL DEPRESSION.

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 100


POSTANESTHETIC HYPOTENSION, DELIRIUM AND HEADACHE ARE MORE FREQUENT THAN AFTER THE USE OF OTHER AGENTS.

Goodman, L.S., and A. G. Gilman. (eds.). The Pharmacological Basis of Therapeutics. 4th ed. New York: Macmillan Co., 1970., p. 77


PUPILLARY SIZE TENDS TO INCREASE BOTH DURING PROFOUND ANESTHESIA & DURING EMERGENCE... LACRIMATION MAY OCCUR... EYEBALL MOVEMENTS USUALLY OCCUR IN PLANE 1... AT PROFOUND LEVELS PROPTOSIS IS COMMON. ... ARTERIAL BLOOD PRESSURE IS USUALLY LITTLE AFFECTED BY CONCN OF CYCLOPROPANE CAUSING SURGICAL ANESTHESIA, ALTHOUGH SEVERE REDN MAY OCCUR WHEN HEMORRHAGE, MYOCARDIAL DISEASE, OR SEPSIS IS PRESENT.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 85


For more Drug Warnings (Complete) data for CYCLOPROPANE (7 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anesthetics

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site. (See all compounds classified as Anesthetics.)


5.2 Absorption, Distribution and Excretion

CYCLOPROPANE IS RAPIDLY ABSORBED AND ALMOST ENTIRELY ELIMINATED BY WAY OF THE LUNGS; A SMALL AMT DIFFUSES THROUGH THE SKIN AND AN ADDITIONAL SMALL AMOUNT (ROUGHLY 0.5%) IS METABOLIZED IN THE BODY...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 87


5.3 Metabolism/Metabolites

...A SMALL AMT (ROUGHLY 0.5%) IS METABOLIZED IN THE BODY AND EXCRETED AS CARBON DIOXIDE AND WATER...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 87


NON-STEADY STATE METABOLISM OF INHALATION ANESTHETICS DURING ANESTHESIA & RECOVERY WAS SIMULATED WITH LINEAR & NON-LINEAR WHOLE BODY COMPARTMENTAL MODEL. THESE TWO MODELS WERE STUDIED FOR NINE ANESTHETICS DURING 1 MINUTE ALVEOLAR CONCN ANESTHESIA LASTING 1, 4 AND 8 HR AND RECOVERY FROM 5 TO 10 DAYS. BOTH MODELS DEMONSTRATED SIGNIFICANT METABOLISM FOR SEVERAL DAYS FOLLOWING ANESTHESIA. FOR THE LINEAR MODEL, BOTH THE PERCENTAGE AND THE MOLAR QUANTITY OF ANESTHETIC METABOLIZED INCREASED WITH INCREASED DURATION OF ANESTHESIA, INCREASED ANESTHETIC FAT SOLUBILITY AND INCREASED ASSUMED RATE OF HEPATIC METABOLISM. FOR THE NON-LINEAR MODEL, THE DURATION OF ANESTHESIA HAD LITTLE EFFECT ON THE PERCENTAGE METABOLIZED BUT DEMONSTRATED INCREASED MOLAR QUANTITIES OF ANESTHETIC METABOLIZED WITH INCREASED DURATION OF ANESTHESIA AND INCREASED FAT SOLUBILITY.

PMID:836747 FEINGOLD A, HOLADAY DA; BR J ANAESTH 49 (2): 155-62 (1977)


5.4 Mechanism of Action

The effect of several inhalation and iv anesthetics, alone or in combination, on brain electric activity during evoked cortical response was studied in rats. All of the anesthetics affect the evoked sensory response in a manner which suggests a common site of anesthetic action, namely, the perturbation of normal modulation exerted upon the ventrobasal thalamus by the thalamic reticular nucleus which is remarkably susceptible to the action of these agents.

Angel A, Gratton DA; Prog Anesthesiol 3 (Pharmacol Basis Anesthesiol): 1-12 (1983)