01-20-01 15:38
No 161914
      Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

I was going throught the merck when I came across this item which I thought was quite interesting. The substance is Lefetamine also known as

Below is the structure.

It says that it is a centrally acting analgesic with sterochemical resemblance to morphine.
K. Ogiu et. al., J. Pharm. Soc. Japan 80, 283 (1960)

NMR data indicate that it is the eclipsed conformation which seems to enhance stereoselctivity for morphine receptors.
T. Sasaki et. al., J. Med Chem. 9, 847 (1966)

If you have a Merck 12th edition check out pg. 5453.

Lefetamine HCl b.p. 218 deg. C
Lefetamine free base b.p. 142 to 147 deg. C

This has a tade name of Santenol or SPA.

Therapeutic catagory: Analgesic

I am wondering if this would be a non-drowsy opiate regarding its structure. I might have to do beilstein search on this item.

I have said it before that if you look at all of the naturally opiates via poppy that they have a structure that includes the amphetamine moiety. It would seem that possibly the d-isomer opiates resemble more the d-amphetamines and that is possibly why DXM kicks your ass the way it does. It is possibly releasing alot of dopamine in conjunction with all the other receptors it binds with creating its well known effects. One other possible effect of opiates is that they could cause a inhibition of the enzyme responsible for endorphan breakdown while also causing endorphan release similar to how PIMA causes the release of dopamine and inhibits the MAO enzyme responsible for the breakdown of monoamines.

One other interesting item is that it is not classified in the merck as a controlled substance but under the designer drug laws it probally is just the same as any other analogs.

(Hive Bee)
01-21-01 09:54
No 168705
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

Drug Alcohol Depend. 1989 Oct;24(2):95-101.
Lefetamine: new abuse of an old drug--clinical evaluation of opioid activity.

Mannelli P, Janiri L, De Marinis M, Tempesta E

Dept. of Psychiatry, Faculty of Medicine, Catholic University of The Sacred Heart, Rome, Italy.

Lefetamine (SPA) combining amphetamine with opioid-like effects, a drug of wide abuse in Japan in the fifties, has now been introduced as such in Italy. In this study the drug was tested to verify its resemblance to opiates. Ten lefetamine abusers were hospitalized and then subjected to naloxone- and pentazocine-tests and detoxified. Moreover, lefetamine was administered to ten opiate addicts with an acute withdrawal syndrome and to ten methadone-treated addicts. The naloxone-test was positive and pentazocine could be substituted for lefetamine. Lefetamine was able to relieve opiate withdrawal and did not precipitate withdrawal symptoms in stabilized opiate addicts. It is concluded that lefetamine may act as an opioid partial agonist.

Farmaco. 1989 Sep;44(9):763-77.
Synthesis, neuropsychopharmacological effects and analgesic-antiinflammatory activities of pyrrole analogues of lefetamine.

Massa S, Stefancich G, Artico M, Corelli F, Silvestri R, Pantaleoni GC, Fanini D, Palumbo G, Giorgi R

Dipartimento di Studi Farmaceutici, Facolta di Farmacia, Universita degli Studi di Roma La Sapienza, Italy.

The synthesis of pyrrole analogues of the analgesic drug lefetamine is reported. These derivatives bear the 1-phenyl-2-(1H-pyrrol-1-yl)ethylamino moiety. Compounds were evaluated for analgesic activities in mice by the hot plate and Randall-Selitto tests. Antiinflammatory activity was tested by the carrageenan-induced rat paw edema method. General neuropsychopharmacological effects were also screened. The most interesting compound, N,N-dimethyl-1-phenyl-2-(1H-pyrrol-1-yl)ethylamine, showed an analgesic effect comparable to that of lefetamine, but devoid of the neurotoxicity of this drug.

Br J Addict. 1989 Jan;84(1):89-95.
Lephetamine abuse and dependence: clinical effects and withdrawal syndrome.

Janiri L, Mannelli P, Pirrongelli C, Lo Monaco M, Tempesta E

Lephetamine (L-SPA) is a compound with central analgesic and anti-inflammatory action, recently reported to be abused in Italy. In this study, cases of L-SPA abuse were recorded. The survey included 15 patients who were assessed for effects caused by using L-SPA and induced by withdrawal. Moreover L-SPA was administered to 15 volunteers. L-SPA displayed effects partly similar to opiates and its withdrawal caused both subjective and objective symptoms. It is concluded that L-SPA exhibits abuse liability and dependence potential of a certain degree.

Pharmacol Res Commun 1985 May;17(5):471-8
Opioid activity of lefetamine.

De Montis MG, Devoto P, Bucarelli A, Tagliamonte A

In mice lefetamine, at the dose of 50 mg/kg produces motor hyperactivity and at the dose of 60 mg/kg produces analgesia. Both effects are abolished by naloxone. Displacement studies by using [3H]-Naloxone (Nx), [3H]-D-Ala-Met-Enkephalinamide (DAMA) and [3H]-Ethylketocyclazocine (EKC) showed that lefetamine competes with all these opiates with an affinity 50 times lower than that of morphine. The displacing capacity of lefetamine is decreased in the presence of 50 mM Na+. It is concluded that lefetamine is an opioid agonist.

Neuropharmacology 1989 Dec;28(12):1405-10

Dual effects of lephetamine on spontaneous and evoked neuronal firing in the somatosensory cortex of the rat.

Janiri L, Persico AM, Tempesta E

Department of Psychiatry and Psychology, Catholic University of the Sacred Heart, Rome, Italy.

Lephetamine is a central analgesic, recently shown to be abused by drug addicts and to induce dependence in humans. The drug was applied microiontophoretically on single neurones of the somatosensory cortex of the rat in vivo. Its activity on the spontaneous and evoked firing rate was recorded. Morphine and naloxone were employed to verify the hypothesis that a mu-opiate mechanism of action could be involved. The most frequent response evoked by lephetamine was a dose-dependent excitation non-reversible by naloxone. On the other hand, units inhibited or apparently unaffected by the drug, showed a selective anti-glutamate (and partly anti-acetylcholine) effect, which was reversed by either systemically- or iontophoretically-administered naloxone. Long-lasting (8-12 min) applications of lephetamine caused a progressive desensitization of cortical neurones to the inhibitory and anti-glutamate effect. The inhibitory activity of lephetamine and morphine was additive and an increased neuronal excitability was shown by a post-inhibitory rebound of glutamate-induced neuronal activity. The action exerted by lephetamine on glutamate-induced excitations and on postsynaptic excitability, its reversibility by naloxone and the occurrence of acute tolerance allow the conclusion that only the inhibitory effect of lephetamine is mediated by an opioid mechanism. The lephetamine-induced excitations, not reversed by naloxone, are difficult to interpret as opioid-mediated.

Apparently this drug is quite old and has been abused in Japan and Italy. Learn something new every day. I believe synthesis would be quite easy with the corresponding ketone and amine. That would give a mixture of d,l-lefetamine which could possibly have the effects of the analgesic for the l and the dopamine release by the d.

(Newbee / Eraser)
04-05-01 21:59
No 182539
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

"...possibly why DXM kicks your ass the way it does."

i think it's all about some mu.<thats one bad motherfucka'>

have there been any references to the hallucinogenic effects?

"pull the wool over your own eyes"
(Guilty of Contempt)
04-21-01 21:30
No 185813
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

Structurally I would think that one of the steroisomers would have an analgesia effect (coupled with all the other stuff that goes along with opiates) and the other would likely be inhibited from binding well (if at all) with the opiate receptors.  The key on the opiate receptors seems to be that N two carbons away from the benzene ring.  In both the opiate agonists and antagonists that seems to be a common structure (even in the enkephalins).  The fundamental difference between the agonists and antagonists looks (from a brief view of structures) to be of the chirality of the nitrogen.  However, the chirality of the C adjacent to the N would probably (in my opinion) play a role in the molecule being able to set itself into the opiate receptors.

Definitely worth a closer look though...


Six legs good, four legs food.  (pigs 4, sheep 4, bees 6)
(Hive Addict)
04-22-01 13:08
No 185982
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

Want to make an easy!!! analog to this compound.
Look up the structure of Benzoin!!!
The N-methyl variation would be easy.  Reductive amination with nitromethane followed be RP/I (or other choice alpha hydroy reduction schemes)  Bammmm there it is.  If you can aminate with dimethyl amine then you have the actual product.

This could be big.  Foxy hasn't the capacity to experiment he is a theoritician (whatever) at this time and he would bee nervous trying such a compound.  But someone might bee interested.  Shit you could even oxidize the leftover alcohol and have a cathinone analog.  Aminate with ethyl amine, isopropyl amine, propyl amine ect for many analogs.

Granted they may not bee active but?????????

This is exciteing

Do Your Part To Win The War
(Chief Bee)
04-22-01 13:53
No 185995
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

Deoxybenzoin (benzyl phenyl ketone, benzoin with only one carbonyl) is available from most chem supply companies, and is relatively cheap, and definitely not watched. Reductive amination with dimethylamine would give lephetamine. If you want to synthesize the deoxybenzoin yourself, react benzylmagnesium bromide with benzaldehyde to get the alcohol, and oxidize to deoxybenzoin with dichromate or permanganate and go from there.

05-19-01 06:10
No 195627
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

Lefetamine is an opioid(synthetic)not opiate(alkaloids of
poppy).There are only 4 opiates known
1)opium (tincture such as paregoric,laudenum, etc.)
2)codeine (phosphate-apap or asp with codeine,cough syrups)
           sulphate-pure codeine in 1/4,1/2 and 1 grain tab
4)heroin    made from morphine
  lefetamine is listed as a scheudule 4,meaning its abuse
potential is less than that of tylenol with codeine #3
Unless someone has zero tolerance to opiates or oids
they are not gonna find this drug useful or any fun.
(Hive Addict)
05-19-01 12:14
No 195661
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

  lefetamine is listed as a scheudule 4,meaning its abuse
potential is less than that of tylenol with codeine #3
Unless someone has zero tolerance to opiates or oids
they are not gonna find this drug useful or any fun.

I don't think that you can be certain of this just from where it is scheduled. It could be something that has slipped under the radar of the drug police.

(Hive Bee)
05-19-01 14:28
No 195688
      Re: Non-fentanyl analgesic phenethylamine derivitive..  Bookmark   

Well since naloxone reverses its effects it most likely could be fun for someone who enjoys that type of high. Looks like it has been abused in Japan and Italy. Someone muust have thought it was fun there to be abused.