CCK-4

Cholecystokinin tetrapeptide (CCK-4, tetragastrin, Trp-Met-Asp-Phe-NH₂) is a peptide fragment derived from the larger peptide hormone cholecystokinin. Unlike cholecystokin which has a variety of roles in the gastrointestinal system as well as central nervous system effects, CCK-4 acts primarily in the brain as an anxiogenic, although it does retain some GI effects, but not as much as CCK-8 or the full length polypeptide CCK-58.

CCK-4

Clinical data
Other names	Tetragastrin; Cholecystokinin tetrapeptide
Routes of administration	Intravenous
ATC code	None
Pharmacokinetic data
Bioavailability	100%
Metabolism	Plasma protease enzymes
Elimination half-life	13 minutes
Excretion	N/A
Identifiers
IUPAC name (3S)-3-[(2S)-2-amino-3-phenylpropanamido]-3-{[(1S)-1-{[(1S)-1-carboxy -2-(indol-3-yl)ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}propanoic acid
CAS Number	1947-37-1 Y
PubChem CID	446569
ChemSpider	393888 N
UNII	0OL293AV80
ChEBI	CHEBI:137728
CompTox Dashboard (EPA)	DTXSID601027522
Chemical and physical data
Formula	C29H35N5O7S
Molar mass	597.69 g·mol−1
3D model (JSmol)	Interactive image
SMILES CSCC[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)[C@H](Cc2c[nH]c3c2cccc3)N
InChI InChI=1S/C29H36N6O6S/c1-42-12-11-22(33-27(39)20(30)14-18-16-32-21-10-6-5-9-19(18)21)28(40)35-24(15-25(36)37)29(41)34-23(26(31)38)13-17-7-3-2-4-8-17/h2-10,16,20,22-24,32H,11-15,30H2,1H3,(H2,31,38)(H,33,39)(H,34,41)(H,35,40)(H,36,37)/t20-,22-,23-,24-/m0/s1 N Key:RGYLYUZOGHTBRF-BIHRQFPBSA-N N
NY (what is this?)  (verify)

CCK-4 reliably causes severe anxiety symptoms when administered to humans in a dose of as little as 50 μg,^[1] and is commonly used in scientific research to induce panic attacks for the purpose of testing new anxiolytic drugs.^[2][3][4][5] Since it is a peptide, CCK-4 must be administered by injection, and is rapidly broken down once inside the body so has only a short duration of action,^[6] although numerous synthetic analogues with modified properties are known.^{[7][8][9][10][11][12][13][14][15][16][17]}

See also

• Pentagastrin