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(Top) 1 Use 2 Synthesis 3 See also 4 References

Pramocaine

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Pramocaine
Clinical data

Trade names	Analpram HC, Caladryl, Caladryl Clear, Cortane-B, Epifoam, Gold Bond Maximum Relief, Itch-X, Pramosone, Prax, Proctodan-HC, Proctofoam, Tronolane, Vagisil Medicated
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682429
License data	US DailyMed: 8bfeea34-25d5-4721-a17f-d9f1d0084cc3, 81ab7fa7-d9b0-49dc-9782-02f37e588c5e
Routes of administration	Topical, rectal, Vaginal
ATC code	D04AB07 (WHO) C05AD07 (WHO)
Legal status
Legal status	Depends on country, some formulations OTC others Rx only
Identifiers
IUPAC name 4-[3-(4-Butoxyphenoxy)propyl]morpholine
CAS Number	140-65-8^Y hydrochloride: 637-58-1^Y
PubChem CID	4886
DrugBank	DB09345^Y
ChemSpider	4717^Y
UNII	068X84E056 hydrochloride: 88AYB867L5^Y
ChEBI	CHEBI:8357^Y
ChEMBL	ChEMBL1198^Y
CompTox Dashboard (EPA)	DTXSID8040692
ECHA InfoCard	100.004.933
Chemical and physical data
Formula	C₁₇H₂₇NO₃
Molar mass	293.407 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O(c2ccc(OCCCN1CCOCC1)cc2)CCCC
InChI InChI=1S/C17H27NO3/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18/h5-8H,2-4,9-15H2,1H3^Y Key:DQKXQSGTHWVTAD-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Pramocaine (INN and BAN, also known as pramoxineorpramoxine HCl) is a topical anesthetic discovered at Abbott Laboratories in 1953^[1] and used as an antipruritic. During research and development, pramocaine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent.^[1] Pharmacologic study revealed it to be potent and of low acute and subacute toxicity, well tolerated by most mucous membranes and of a low sensitizing index in humans.^[1] Like other local anesthetics, pramocaine decreases the permeability of neuronal membranes to sodium ions, blocking both initiation and conduction of nerve impulses. Depolarization and repolarization of excitable neural membranes is thus inhibited, leading to numbness.

Use[edit]

Topical anesthetics are used to relieve pain and itching caused by conditions such as sunburn or other minor burns, insect bites or stings, poison ivy, poison oak, poison sumac, and minor cuts and scratches.^[2] The popular itch creams Gold Bond and some forms of calamine lotion use pramocaine hydrochloride to numb sensitive skin, as does the pain relief variant of Neosporin and some formulations of Sarna. The hydrochloride salt form of pramocaine is water-soluble.

Pramocaine is a common component of over the counter hemorrhoid preparations.

Pramocaine is also included in some topical antibiotics like Neosporin Plus Pain Relief used to treat or prevent infections due to its pain relieving effects. However, there is no additional antibiotic effect compared to antibiotics without pramocaine.^[3]

Synthesis[edit]

Patent:^[4] Sino:^[5]

The ether formation between hydroquinone (1) and 1-bromobutane (2) gives 4-butoxyphenol [122-94-1] (3). Alkylation with 4-(3-chloropropyl)morpholine [57616-74-7] (4) gives pramocaine (5).

References[edit]

^ ^a ^b ^c Schmidt JL, Blockus LE, Richards RK (1953). "The Pharmacology of Pramoxine Hydrochloride: A New Topical Local Anesthetic". Current Researches in Anesthesia & Analgesia. 32 (6:1): 418–25. PMID 13107298.