Pyrrocaine

Pyrrocaine
Names
	Preferred IUPAC name N-(2,6-Dimethylphenyl)-2-(pyrrolidin-1-yl)acetamide
Identifiers
CAS Number	2210-77-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1895219;
ChemSpider	22776;
EC Number	218-642-7;
KEGG	D05665;
PubChem CID	24361;
UNII	9D47L94CPW;
CompTox Dashboard (EPA)	DTXSID9046150 ;
	InChI InChI=1S/C14H20N2O/c1-11-6-5-7-12(2)14(11)15-13(17)10-16-8-3-4-9-16/h5-7H,3-4,8-10H2,1-2H3,(H,15,17) Key: OYCGKECKIVYHTN-UHFFFAOYSA-N;
	SMILES Cc1cccc(c1NC(=O)CN2CCCC2)C;
Properties
Chemical formula	C14H20N2O
Molar mass	232.327
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pyrrocaine is a local anesthetic drug. The cogency of pyrrocaine is equivalent to lidocaine in blocking the motor nerve and sensory. Pyrrocaine was proven to be somewhat harmless compared to lidocaine. No signs of methemoglobinemia was found while observing. It was considered unsafe for acute porphyria treatment. No evidence is found that it is profitly used now.^[1]

History

In the 1960s it was most of the time used as a nerve blocker dental anesthetic and dentists recommended it due to its fast commencement.^[1]

Adverse effects

Pyrrocane has very similar side effects on blood pressure and heart rate compared to lidocaine.^[2]

Synthesis

Selfsame as lidocaine, albeit interposing pyrrolidine for diethylamine.

Amide formation between 2,6-Dimethylaniline (1) and Chloroacetyl chloride (2) gives [1131-01-7] (3). Displacement of the remaining halogen by pyrrolidine (4) completed the synthesis of Pyrrocaine (5).

References

^ ^a ^b "NCATS Inxight: Drugs". drugs.ncats.io. Retrieved 2018-08-07.
^ Annals of Dentistry. New York Academy of Dentistry. 1983.
^ Löfgren, Nils; Tegnér, Claës; Takman, Bertil (1957). "Studies on Local Anesthetics. XVI.". Acta Chemica Scandinavica 11: 1724–1737. doi:10.3891/acta.chem.scand.11-1724.
^ US 2813861, Schlesinger, Albert & Gordon, Samuel M., "Pyrrolidino-2, 6-dimethyl anilide salt of 8-[2'-methoxy-3'-(7-theophyllinyl mercuri)] propyl-coumarin-3-carboxylic acid", published 1957-11-19, assigned to Endo Laboratories, Inc.
^ GB 986993, "Local anesthetics", published 1965-03-24, assigned to Graham Chemical Corp.

[:0-1] "NCATS Inxight: Drugs". drugs.ncats.io. Retrieved 2018-08-07.

[2] Annals of Dentistry. New York Academy of Dentistry. 1983.

[3] Löfgren, Nils; Tegnér, Claës; Takman, Bertil (1957). "Studies on Local Anesthetics. XVI.". Acta Chemica Scandinavica 11: 1724–1737. doi:10.3891/acta.chem.scand.11-1724.

[4] US 2813861, Schlesinger, Albert & Gordon, Samuel M., "Pyrrolidino-2, 6-dimethyl anilide salt of 8-[2'-methoxy-3'-(7-theophyllinyl mercuri)] propyl-coumarin-3-carboxylic acid", published 1957-11-19, assigned to Endo Laboratories, Inc.

[5] GB 986993, "Local anesthetics", published 1965-03-24, assigned to Graham Chemical Corp.

[1]

[2]

[3]

[4]

[5]

History

Adverse effects

Synthesis

See also

References