L-Lysine is an essential amino acid in human diet.

L-Lysine is metabolised in mammals to give acetyl-CoA, via an initial transamination with α-ketoglutarate.

Piperidine Production

Tests conducted using mice showed that the conversion of lysine into piperidine was observed only in the kidneys and large intestines (colon). The latter is probably caused by the intestinal flora. Formation of cadaverine and pipecolic acid from lysine was observed in the brain, liver, kidney, and large intestine. In addition, pipecolic acid was formed in the heart.[1][2]

It can take 3 or more hours for food to reach the colon (this varies dramatically from person to person, and depends highly on other contents in the digestive system). For this reason excess L-lysine supplements will not normally begin to produce piperidine until several hours have passed.

Herpes Simplex Virus (HSV)

Some studies have found that taking lysine on a regular basis may help prevent outbreaks of cold sores and genital herpes.


12 mg/kg/day for adults.
When used during an active herpes flare up 3,000 - 9,000 mg/day is a common adult dose.

Side Effects

Side-effects are rare with lysine supplements, although a few cases of abdominal cramps and diarrhea have been reported with very high doses (more than 10gm per day).

Chemical Properties

PubChem Compound ID: 5962
Molecular Weight: 146.18756 [g/mol]
Molecular Formula: C6H14N2O2
XLogP3: -3
IUPAC Name: (2S)-2,6-diaminohexanoic acid
InChI: InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,
Canonical SMILES: C(CCN)CC(C(=O)O)N
Isomeric SMILES: C(CCN)C[C@@H](C(=O)O)N

See Also

1. T. Schmidt-Glenewinkel, Y. Nomura, E. Giacobini;
The conversion of lysine into piperidine, cadaverine, and pipecolic acid in the brain and other organs of the mouse; Neurochemical Research; December 1977, Volume 2, Issue 6, pp 619-637; DOI 10.1007/BF00963776; ISSN 0364-3190
2. Nomura Y, Schmidt-Glenewinkel T, Giacobini E, Ortiz J;
Metabolism of cadaverine and pipecolic acid in brain and other organs of the mouse; J Neurosci Res. 1983;9(3):279-89; PubMed PMID: 6406679
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