Home > Oxytocin (Molecule of the Month for June 2007 )

Picture of Oxytocin

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Oxytocin structure
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Picture of Oxytocin

C43 H66 N12 O12 S2

Oxytocin is a mammalian hormone that also acts as a neurotransmitter in the brain. In women, it is released mainly after distension of the cervix and vagina during labor facilitating birth, and also after stimulation of the nipples helping breastfeeding. Oxytocin is released during orgasm in both sexes. In the brain, oxytocin is involved in social recognition and bonding, and might be involved in the formation of trust between people. Injected oxytocin analogues are used to induce labour and support labour in case of non-progression of parturition. It has largely replaced ergotamine as the principal agent to increase uterine tone in acute postpartum haemorrhage.

Oxytocin is a peptide of nine amino acids (a nonapeptide). The sequence is cysteine - tyrosine - isoleucine - glutamine - asparagine - cysteine - proline - leucine - glycine. The cysteine residues form a sulfur bridge. The structure of oxytocin is very similar to that of vasopressin. Oxytocin and vasopressin were discovered, isolated and synthesized by Vincent du Vigneaud in 1953, work for which he received the Nobel Prize in Chemistry in 1955.

Uterine contraction important for cervical dilation before birth and causes contractions during the second and third stages of labor. Oxytocin release during breastfeeding causes mild but often painful uterine contractions during the first few weeks of lactation. This also serves to assist the uterus in clotting the placental attachment point postpartum. Letdown reflex in lactating (breastfeeding) mothers, oxytocin acts at the mammary glands, causing milk to be 'let down' into a collecting chamber, from where it can be extracted by sucking at the nipple. Sucking by the infant at the nipple is relayed by spinal nerves to the hypothalamus. The stimulation causes neurons that make oxytocin to fire action potentials in intermittent bursts; these bursts result in the secretion of pulses of oxytocin from the neurosecretory nerve terminals of the pituitary gland.

Formal Chemical Name (IUPAC)
(S)-N-((S)-1-(2-amino-2-oxoethylamino)-4-methyl-1-oxopentan-2-yl)-1-((4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-sec-butyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-ca

References

http://en.wikipedia.org/wiki/Oxytocin

Update by Karl Harrison
(Molecule of the Month for June 2007 )