It07:Morphine

It07:Morphine
General
Systematic name	7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol
Molecular formula	C17H19NO3
SMILES	CN5CC[C@]23C1=C4C=CC(O)=C1O[C@H]2[C@@H](O)C=C[C@]([H])3C[C@@H]45
Molar mass	285.34 g/mol
Appearance	White Powder/Pills/Colourless liquid
CAS number	57-27-2
Properties
Density & phase	{{{Density}}} g/cm³
Solubility in water	{{{Sol_Water}}} g/100 ml (25°C)
Melting point	{{{Mp}}} K
Boiling point	{{{Bp}}} K
Acidity (pKa)	{{{pKa}}}
Basicity (pKb)	{{{pKb}}}
Chiral rotation [α]D	{{{Rotation}}}°
Viscosity	{{{Viscosity}}} cP at 25°C
Structure
Molecular shape	{{{Mol_Shape}}}
Coordination geometry	{{{Coordination}}}
Crystal structure	{{{Crystal_Structure}}}
Dipole moment	{{{DM}}} D
Hazards
MSDS	External MSDS
Main hazards	{{{Hazards}}}
NFPA 704	{{{NFPA}}}
Flash point	{{{Fp}}}°C
R/S statement	R: {{{R-S}}} S: ?
RTECS number	{{{RTECS}}}
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Other anions	{{{Other_anion}}}
Other cations	{{{Ohter_cation}}}
Related compounds	{{{Relative_Compounds}}}
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Structure
Molecular shape	{{{MolShape}}}
Coordination geometry	{{{Coordination}}}
Crystal structure	{{{CrystalStruct}}}
Dipole moment	{{{Dipole}}} D

Vas_morphine.pdb

Introduction

Morphine is the main biologically active derivative of opium, which is extracted from the Papaver somniferum species of poppy. Its narcotic effect on the nervous system has led to its widespread use as an intense pain killer in hospitals and other medical care. As it is a powerful drug, it sometimes produced side-effects such as impairment of physical and mental performance, decrease in hunger, and inhibition of the cough reflex. In women it can cause disruption to the mentstrual cycle.

Addiction and Withdrawal

Being and opiate, it is very similar in structure to heroin, and thus gives rise to similar biochemistry, resulting in feelings of euphoria, and significantly reduced feelings of fear and anxiety. It is highly addictive, and both psycological and physical dependence can ensue quickly. Withdrawal symptoms include diarrhoea, stomach cramps and insomnia amongst others.

Synthesis

Morphine can be synthesised either biologically or via numerous artificial methods. The biological pathway begins with the amino acid L-tyrosine, which is converted through 2 steps into (S)-norcoclaurine. This is then alkylated to give a product called (S)-reticuline, which is oxidised to form a 1,2 dehydroreticulinium salt the salt is then reduced, and the stereocentre inverted, by hydrogenation using the naturally occuring molecule NADPH, which is then oxidised to NADP. The desired product from this reaction (R)-reticuline, is unstable due to phenolic coupling, and quickly forms salutaridine. A reduction of the ketone group then ensues, converting the product into salutaridinol which can then undergo S_N2 in acidic conditions. The mechanism for this process is shown below:

The methoxy group is then converted from an ether into a ketone group to form neopinone. A proton transfer then occurs to form codeinone before the newly formed ketone group is reduced to a hydroxyl group. This final product is Morphine. The full synthesis is displayed below.

The landmark artificial synthetic method was developed by M.J. Gates and since then other syntheses such as the Rice synthesis and Overman synthesis amongst others have been developed and used to synthesise morphine from a variety of starting materials.

History

Used as a pain relief medicine during the American Civil War, morphine was widely employed, resulting in many soldiers having the 'war disease' morphine addiction when the war ended. In its early life it was prescribed by some physicians to cure the problem of alcohol addiction, as morphine was considered to be less harmful to the body, and produced less anti-social behaviour. Despite being made illegal in the UK by the Harrison Narcotics Act in 1914, morphine remained a popular recreational drug until heroin was developed (originally as a cure for morphine addiction).

Spectroscopic Data

Infra-red Spectrum

Mass Spectrum