m-cylcohexyloxy-a-phenethylamine

[frankblank]

It seems like a pretty simple compound and this paper says it is an opioid agonist. Ive tried to get more information on it but cant find any. Does anyone know if this is a dead end? Is there a common name for this compound or class of compounds? thanks.

The paper reads in part:

SOME MORPHINE-LIKE PROPERTIES OF (+)-CYCLOHEXYLOXY-
ALPHA-PHENYLETHYLAMINES
BY
A. McCOUBREY
From the Biochemical Laboratories, Institute of Psychiatry (British Postgraduate Medical Federation,
University of London), Maudsley Hospital, S.E.5
(RECEIVED JULY 1, 1952) In contrast to


unlike b-phenylethylamines, few a-phenylethylamines
have been found to be analgesic. Like pethidin
and amidone, m-cyclohexyloxy a-phenylethyl
amine shows a formal resemblance to structure
present in the morphine molecule.


1. m- and p-cycloHexyloxy-a-phenylethylamine
show qualitative similarity to morphine in anal-
gesic activity, respiratory depression, effect on body
temperature and blood pressure. No consistent
response was obtained for blood sugar changes.

2. m- and p-isoPropyloxy- and p-ethoxy-a-
phenylethylamine have no analgesic activity and,
apart from respiratory depression their pharma-
cological properties are different from those of the
cyclohexyl ethers and morphine.

3. Evidence was obtained to show that the anal-
gesic effect of the cyclohexyloxy-a-phenylethyl-
amines is more nearly related to that of morphine,
amidone, and pethidine than to the chemically
analogous antipyretic and analgesic phenacetin.

 

[mad_scientist]

Good find, but fuck that, only 1/3rd the potency of morphine and

The m-cyclohexyl ether was not examined fully because of its pronounced tendency to produce local necrosis.

 

[frankblank]

okay i missed that. thanks

 

[dread]

pronounced tendency to produce local necrosis

ewwwwwwwwww

(I meant to type that in caps but the board won't let me)

 

[frankblank]

i just thought if m-cycloxexyloxybenzaldehdye was easy to source from china, and the henry reaction worked on that. that would be a really simple opioid synth. now that i read it again, it does look like a pretty bad drug. thanks.

 

[Smokey McPot]

are there any other subbed-alpha-phenethylamines that have a better effects profile that are active in this way?

 

[frankblank]

i dont know much about it. it did say that cessation did not induce withdrawl symptoms. and i didn't see that they know for sure if its orally active. It could be very dysphoric like metazocine. I couldnt find much information on it. but all i used was google.

 

[fastandbulbous]

are there any other subbed-alpha-phenethylamines that have a better effects profile that are active in this way?

Lefetamine is effectively an alpha PEA, so all derivatives would git the bill

 

[Hammilton]

yeah, and a beta phenethylamine.

Unless one is injecting, there's no worry about the local necrosis thing, I believe. It's not the only compound to have such problems IV, of course.

 

[nuke]

Watch the synthesis discussion...

As it's a phenethylamine and phenethylamines often get munched up quickly in the body, I kind of wonder what the pharmacokinetics are like.