MORPHINE - (57-27-2)

Introduction

Name: morphine; (5α,6α)-7,8-didehydro- 4,5-epoxy-17-methylmorphinan-3,6-diol
* IUPAC
CAS Number: 57-27-2
Chemical Formula: C17H19NO3
Molar Mass: 285.33766 g
Mass Percent: C 71.557 %; H 6.7116 %; N 4.9088 %; O 16.821 % 

Classification

Uses/Function

• "Morphine is an alkaloid present in opium, and is probably the most effective drug for the relief of extreme pain...Because of the adverse habit-forming characteristic of morphine, certain synthetic substitutes have been sought." 1

• "Morphine ans its relatives, widely used as painkillers in developed countries, can be fairly expensive and are often taken for extended periods of time." 2

• "Analgesic...Morphine relieves pain, but it also constipates and suppresses the urge to cough...Morphine was widely used during the American Civil War both for relieving pain of battle wounds and for controlling diarrhea...The more potent opioid analgesics - morphine, codeine, and heroin - moderate the brain's perception of pain by binding to receptor sites on neurons in the central nervous system." 3

• "Analgesic (narcotic), preanesthetic, antitussive, antiperistaltic." 4

Physical Properties

Melting Point:*
255°C 5 = 528.15 K = 491°F


* - 1 atm pressure

Solubility

Qualitative:
very soluble: benzene • acetone • ethyl ether • chloroform 5

Bonding

Double Bonds: 4
Triple Bonds: 0
σ Bonds: 44
π Bonds: 4
Total: 48
Carboxyl Groups: 0
Hydroxyl Groups: 2
Hybridization: single bonded carbons, oxygens, and nitrogens are sp3; double bonded carbons are sp2

For More Information

Sources

(1) - Estok, George K. Organic Chemistry: A Short Text; W.B. Saunders: Philadelphia, 1959; p 241.
(2) - Ehrenberg, Rachel. Chemists Pin Down Poppy's Tricks for Producing Narcotic Painkiller. Science News, April 10, 2010, p 5.
(3) - Suchocki, John. Conceptual Chemistry: Understanding Our World of Atoms and Molecules; Addison Wesley: San Francisco, California, 2001; pp 438, 476.
(4) - The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed.; Budavari, S.; O'Neil, M.J.; Smith, A.; Heckelman, P. E.; Kinneary, J. F., Eds.; Merck & Co.: Whitehouse Station, NJ, 2001; entry 6300.
(5) - Lide, David R. CRC Handbook of Chemistry and Physics, 83rd ed.; CRC Press: Boca Raton, FL, 2002; p 3-211.