Thiambutenes Japanese Veterinary Opioids

[Paregoric Kid]

does anyone have any info on these drugs? I've read that they are related to the diaryl opioids (methadone, LAAM, propoxyphene, etc.) I've heard they should not be too difficult to synthesize.

Dimethylthiambutene
CAS Registry Number: 524-84-5
CAS Name: N,N-Dimethyl-4,4-di-2-thienyl-3-buten-2-amine
Additional Names: N,N,1-trimethyl-3,3-di-2-thienylallylamine; 3-dimethylamino-1,1-bis(2-thienyl)-1-butene; 3-dimethylamino-1,1-di(2¢-thienyl)but-1-ene
Manufacturers' Codes: 338C48; NIH-4542
Trademarks: Ohton; Aminobutene; Dimethibutin; Kobaton; Takaton

Ethylmethylthiambutene
CAS Registry Number: 441-61-2
CAS Name: N-Ethyl-N-methyl-4,4-di-2-thienyl-3-buten-2-amine
Additional Names: N-ethyl-N,1-dimethyl-3,3-di-2-thienyl-2-propenamine; N-ethyl-N,1-dimethyl-3,3-di-2-thienylallylamine; 3-ethylmethylamino-1,1-di(2¢-thienyl)but-1-ene; ethylmethiambutene
Manufacturers' Codes: 1C50; NIH-5145
Trademarks: Emethibutin

Thiambutene
CAS Registry Number: 86-14-6
CAS Name: N,N-Diethyl-1-methyl-3,3-di-2-thienylallylamine
Additional Names: 3-diethylamino-1,1-di(2¢-thienyl)but-1-ene; diethylthiambutene
Manufacturers' Codes: 191C49; NIH-4185

Tipepidine
CAS Registry Number: 5169-78-8
CAS Name: 3-(Di-2-thienylmethylene)-1-methylpiperidine
Additional Names: 1-methyl-3-piperidylidenedi(2-thienyl)methane; tipedine
Manufacturers' Codes: AT-327; CR-662

[superman]

those compounds are useless as they are not opiods. however 2-Bromothiophene (tipepidine) is used in the synthesis of TCP, a phencyclidine analog.

given that TCP was produced clandestinely three decades ago and has been banned, so you'll probably have some trouble getting larger quanities of this compound.

so ya, no morphine killers in this list

[Paregoric Kid]

what the hell are you talking about? they are opioids take another look at the structures. they are scheduled in many countries and share structural similarities to methadone, if it isn't an opioid how does it create analgesia? the japanese use thiambutene compounds as veterinary analgesics. I've read papers that say specifically dimethylthiambutene and ethylmethylthiambutene are mu agonists. right now I've only found a patent and some research papers that talk about it as an opioid but if you also go to wikipedia and look under the opioid analgesics in the box at the bottom http://en.wikipedia.org/wiki/Analgesic and you will see dimethylthiambutene and ethylmethylthiambutene under the opioid category.

really where do you get off saying they are not opioids?

I quote from fastnbulbous, a mod over at bluelight,
""The Morphine Rule:"
I] A phenyl or aromatic ring.
II] A quaternary carbon atom.
III] A CH2-CH2 group.
IV] The CH2-CH2 group must be attached to a tertiary nitrogen atom.

They are not thatstrict a set of rules really; fentanyl fails on rule II and dimethylthiambutene fails on rules II & III (and by inference rule IV) yet was added to the UK's Misuse of Drugs act because of abuse in Japan where it's used in vetinary medicine.
They're a pretty good set of guidelines, but aren't watertight."

"There are much more unusual opioids that don't so much break the above skeletal structural requirements, but bend them very severely, good examples being dimethylthiambutene and etonitazene. There are some compounds that you'd never guess were mu agonist opioids at an initial glance, but that on further examination do again 'sort of' conform to something like the above skeleton. On initial viewing, 2-(dimethylamino)ethyl O-ethylbenzilate (dimenoxadrol) looks like it should be an anticholinergic or antihistaminic drug due to similarities to other drugs of those two groups, but is in fact primarily a mu agonist as evidenced by it's status as a class A drug in the UK (if you look closely you start to see a lot of similarities with the opioid based on the structure of methadone)."
speaking of bluelight here are some threads over there that mention the thiambutene compounds:
Unusual Opiates: http://www.bluelight.ru/vb/showthread.php?t=276949
Japanese vet. analgesics: http://www.bluelight.ru/vb/showthread.php?t=217848 (http://www.bluelight.ru/vb/showthread.php?t=217848)
Safest methadone dose: http://www.bluelight.ru/vb/showthread.php?t=210236&page=2

Diethylthiambutene, Dimethylthiambutene, Ethylmethylthiambutene are schedule I in the US CSA, however I did not see thiambutene or tipepidine.

[Paregoric Kid]

take a look at the diphenylpropylamine derivatives and compare. for example compare tipepidine and dextromoramide and you will start to see the similarities.
some of the diphenylpropylamine derivates include: Dextropropoxyphene, Dextromoramide, Bezitramide, Piritramide. and then the phenylheptylamines like methadone, LAAM, alpha- d-acetylmethadol, beta- d-acetylmethadol.

also the dea says it is a opioid drug http://www.dea.gov/pubs/scheduling.html they have a column on the schedules called non-narcotic and if a drug is not a narcotic (an opioid) there is an N in that column to indicate so.

[repeek]

Found this in a paper on the subject:

J. A. Krahenmann1
(1) Veterinär-Anatomisches Institut, Universität Zürich, Winterthurerstr. 260, 8057 Zürich, Switzerland
Received: 10 October 1968
Abstract Of the ultra-short- and short-acting barbiturates thiopentone sodium and pentobarbitone sodium require higher dosages for sugical procedures in the dog, sheep and goat in a temperate climate (Zürich, Munich, Liverpool) than in a tropical climate (Khartoum, Sudan). This also applies to the morphium derivative thiambutene-HCl in the dog. The relationship is reversed for methadone-HCl, for which an up to 50% higher dose was needed in Khartoum and apparently is brought about by a complex physico-chemical mechanism, the dynamics of which require further investigation.



Seems it is very short acting and very potent, Bow....wow:)