Camylofin

Camylofin is an antimuscarinic drug.^[1]

Camylofin

Clinical data
Other names	Acamylophenine
AHFS/Drugs.com	International Drug Names
ATC code	A03AA03 (WHO)
Identifiers
IUPAC name Isopentyl 2-[2-(diethylamino)ethylamino]-2-phenylacetate
CAS Number	54-30-8 Y
PubChem CID	5902
ChemSpider	5691 Y
UNII	340B6Q764V
ChEMBL	ChEMBL253592 N
CompTox Dashboard (EPA)	DTXSID7046415
ECHA InfoCard	100.000.184
Chemical and physical data
Formula	C19H32N2O2
Molar mass	320.477 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OCCC(C)C)C(NCCN(CC)CC)c1ccccc1
InChI InChI=1S/C19H32N2O2/c1-5-21(6-2)14-13-20-18(17-10-8-7-9-11-17)19(22)23-15-12-16(3)4/h7-11,16,18,20H,5-6,12-15H2,1-4H3 N Key:RYOOHIUJEJZCFT-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Camylofin is a smooth muscle relaxant with both anticholinergic action and direct smooth muscle action. Anticholinergic action is produced by inhibiting the binding of acetylcholine to muscarinic receptors, but the action is less pronounced.^{[citation needed]} Direct smooth muscle relaxation is achieved by inhibiting phosphodiesterase type IV, which leads to increased cyclic AMP and eventually reduced cytosolic calcium. Thus camylofin has a comprehensive action to relieve smooth muscle spasm. It is used to treat stomach ache in infants and children. Usually it is given in combination with paracetamol to treat stomach ache, as well as pyrexia.^[2]

Synthesis

Synthesis:^[3][4] Patents:^[5][6][7] Metamizole salt patents:^[8][9][10]

The Hell–Volhard–Zelinsky halogenation on phenylacetic acid [103-82-2] (1) gives 2-Bromo-2-phenylacetyl bromide, CID:15621041 (2). Treatment with isoamyl alcohol [123-51-3] gives 3-methylbutyl bromo(phenyl)acetate [92018-48-9] (3). Alkylation with N,N-Diethylethylenediamine [100-36-7] (4) completed the synthesis of Camylofin (5).

References

1. "Camylofin". PubChem. Retrieved 2019-06-02.
2. Sarbhjit K, Bajwa SK, Parmjit K, Surinder B (September 2013). "To compare the effect of camylofin dihydrochloride (anafortin) with combination of valethamate bromide (epidosin) and hyoscine butyl-N-bormide (buscopan) on cervical dilation". Journal of Clinical and Diagnostic Research. 7 (9): 1897–9. doi:10.7860/JCDR/2013/6231.3345. PMC 3809631. PMID 24179892.
3. Bruzzese, Tiberio; Crescenzi, Elda (1966). "N-Aminoalkyl-α-aminoacids and Their Corresponding Ethyl Esters". Journal of Pharmaceutical Sciences. 55 (7): 737–740. doi:10.1002/jps.2600550717.
4. Szarvasi, E. et al, Bull. Soc. Chim. Fr., 1957, 1019.
5. Brock Norbert, Kuhas Engelbert, & Schmeisser Martin, U.S. patent 2,665,300 (1954 to Asta Medica AG).
6. Martin Dr-Chem Schmeisser, Engelbert Dr Phil Kuehas, Norbert Dr Med Brock, DE842206 (1952 to Asta Werke Ag Chem Fab).
7. , GB688331 (1953 to Asta Medica AG).
8. , GB782068 (1957 to Asta Medica AG).
9. Kuhas Engelbert, Brock Norbert, & Arnold Herbert, CA566251 (1958 to Asta Medica AG).
10. Arnold Herbert, Kuhas Engelbert, & Brock Norbert, U.S. patent 2,857,395 (1958).