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Thread: 1-(3,4-methylenedioxy-phenyl)-2-pyrrolidin-1-yl-pentan-1-one

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    1-(3,4-methylenedioxy-phenyl)-2-pyrrolidin-1-yl-pentan-1-one 
    #1
    Any one have any idea what 1-(3,4-methylenedioxy-phenyl)-2-pyrrolidin-1-yl-pentan-1-one is? If someone could draw that stucture it would help immensely, I'm not sure what this beast looks like and would love to know. Thanks!
     

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    #2
    I read in another thread its possibly a dopamine reuptake inhibitor / stimulant active at around 5mg.. not sure.. i'm interested myself.



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    #3
    Bluelight Crew fastandbulbous's Avatar
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    Yeah, someone that I'm friends with, who used to post at the Hive, was especially interested in cathinone derivatives & from his investigations, the longer alpha-alkyl chain aminoketones are mostly stimulants devoid of any entactogen activity (quite potent stimulants at that). Whether or not the methylenedioxy ring is present doesn't have much effect on the overall action
     

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    #4
    Bluelighter Smyth's Avatar
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    if the methylenedioxy is not even required, then i see no point in having it there - that is my philosophy

    when the chemical architect is adding organic shrubbery to his molecules he at least needs to feel he is doing it for a reason, otherwise it just becomes nonsensical
     

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    #5
    The reason, in my opinion: It seems that people will get excited about and buy anything with a 3,4-methylenedioxy group attached.
     

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    #6
    It kind of scares me seeing this on the RC market... with a dosage of under 1/25 the usual MD- compound dosage. It could be very very dangerous to take an MDMA-like dose of this compound. Please be very careful if researching with it.
     

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    #7
    Originally posted by djfriendly
    The reason, in my opinion: It seems that people will get excited about and buy anything with a 3,4-methylenedioxy group attached.
    I think you have a point there. However, if you look at the pharmacological information in the patent I posted in the other thread, you will notice that this compound is the most potent and the least toxic in this series. So in this case the methylenedioxy is good for something else than just to attract customers.
     

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    #8
    Bluelighter Smyth's Avatar
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    thanks for highlighting this - clearly it is something that i am going to have to investigate. i found the other thread you are referring to.

    It is in German?! This complicates matters somewhat
    Last edited by Smyth; 09-07-2005 at 10:54.
     

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    #9
    There's this

    PDF

    that was posted in that other thread, then i found this,

    Registry Number: 687603-66-3
    Formula: C16 H21 N O3

    CA Index Name: 1-Pentanone, 1-(1,3-benzodioxol-5-yl)-2-(1-pyrrolidinyl)- (9CI)

    Registry Number: 24622-62-6
    Formula: C16 H21 N O3 . Cl H

    CA Index Name: 1-Pentanone,
    1-(1,3-benzodioxol-5-yl)-2-(1-pyrrolidinyl)-, hydrochloride (9CI)

    Other Names: Valerophenone,
    3',4'-(methylenedioxy)-2-(1-pyrrolidinyl)-, hydrochloride (8CI);
    1-(3',4'-Methylenedioxyphenyl)-2-pyrrolidino-1-pentanone hydrochloride

    Bibliographic Information

    1-[(3,4-Methylenedioxy)phenyl]-2-pyrrolidino-1-alkanones as
    stimulants. (Boehringer Ingelheim G.m.b.H.). Brit. (1969),
    7 pp. CODEN: BRXXAA GB 1149366 19690423 Patent written in
    English. Priority: DE 19650523. CAN 72:21608 AN 1970:21608
    CAPLUS

    Patent Family Information

    Patent No. Kind Date Application No. Date
    GB 1149366 19690423

    Priority Application
    DE 19650523

    Abstract

    The title compds. (I) were prepd. by the reaction of a
    3',4'-methylenedioxyphenyl a-haloalkyl ketone with either excess
    pyrrolidine in an inert solvent at <100, or NaOMe then pyrrolidine
    in an inert solvent. Thus, 22.1 g
    1-(3,4-methylenedioxy-phenyl)-4-methylpentan-1-one in 100 ml C6H6 was
    brominated at room temp. with 5.1 ml Br in 15 ml C6H6, then evapd. in
    vacuo; a soln. of the residue in 100 ml C6H6 was treated with 40 ml
    Et2O, then with 12 g pyrrolidine, kept 5 hr at 50, worked up to give
    71% I (R = H, R1 = Pr) HCl salt m. 236-8 (alc.-Et2O). A soln. of
    1.15 g Na in 30 ml MeOH was added to 13.2 g
    1-(3,4-methylenedioxyphenyl)-2-bromo-2-methylpropan-1-one in 20 ml
    dry MeOH, the mixt. refluxed 1 hr worked up and treated with 6 g
    pyrrolidine, then refluxed 17 hr, and worked up to give I (R = R1 =
    Me) b0015 150, HCl salt m. 188-90 (alc.-Et2O). Similarly were
    prepd. the following I (R, R1, and m.p. of HCl salt gi ven): H, Et
    (III), 227-8 (EtOH-Et2O); H, Bu (IV), 205.5-7. 0 (iso-PrOH-Et2O);
    H, Pr (V), 229-31 (iso-PrOH-Et2O); H, H, 234-5; H, Me, 242-3; H,
    C5H11 (VI), 201.5-3.5; H, C6H13, 184.5-6.0; H, iso-Pr, 266-7; H,
    sec-Bu, (HBr salt) 257-8; Me, Pr, (HBr salt) 151-2; Et, Et, (HBr
    salt) 166-7; and also
    3',4'-methylenedioxy-2-morpholinoaceto-phenone, m. 219-20. I, esp.
    II, III, IV, V, and VI, are low toxicity central nervous system
    stimulants, and have hypertensive activity. The stimulation dose,
    LD50, and therapeutic index are for II, 0.20, 175 mg/kg, 875, IV,
    0.54, 250 mg/kg, 463, and V, 0.96, 285 mg/kg, 296, resp., compared
    with benzedrine 1.95, 80 mg/kg, 42, and
    1-(p-tolyl)-2-pyrrolidinopentanone, 1.6, 370 mg/kg, 231, resp.

    Patent Classifications

    IPC: C07D.

    Indexing -- Section 27 (Heterocyclic Compounds (One Hetero Atom)

    Nervous system
    (stimulants for central, (methylenedioxy)pyrrolidinylalkanophenones as)

    Bibliographic Information

    Pyrrolidino ketones. (Boehringer, C. H., Sohn). Fr. M.
    (1967), 5 pp. CODEN: FMXXAJ FR 5502 19671204 Patent written
    in French. Priority: DE 19650528. CAN 72:66801 AN 1970:66801
    CAPLUS

    Patent Family Information

    Patent No. Kind Date Application No. Date
    FR 5502 19671204

    Priority Application
    DE 19650528


    Abstract

    Title compds. were prepd. as central nervous system stimulants.
    1-(3,4-Methylenedioxyphenyl)-4-methyl-1-pentanone (22.1 g) in 100 ml
    C6H6 was brominated with 5.1 ml Br in 15 ml C6H6 at room temp., the
    mixt. evapd., the residue (31.3 g) dissolved in 100 ml C6H6, 40 ml
    Et2O and 12 g pyrrolidone (I) were added, and the mixt. heated 5 hr
    at 50 to give 23 g
    1-(3,4-methylenedioxyphenyl)-2-pyrrolidino-4-methyl-1-pentanone (II);
    HCl salt m. 236-8 (EtOH-Et2O). A soln. of 13.2 g
    1-(3,4-methylenedioxyphenyl)-2-bromo-2-methyl-1-propanone in 20 ml
    MeOH was refluxed 1 hr after addn. of 1.15 g Na in 30 ml MeOH. The
    mixt. was partitioned between H2O and Et2O, the Et2O evapd., and the
    residue refluxed 17 hr with 6 g I to yield
    1-(3,4-methylenedioxyphenyl)-2-pyrrolidino-2-methyl-1-propanone; HCl
    salt m. 188-90 (EtOH-Et2O). Several other compds. were prepd. and
    their phys. consts. given. Biol. test data were given.

    Patent Classifications

    IPC: A61K; C07D.

    Indexing -- Section 27 (Heterocyclic Compounds (One Hetero Atom)

    Ketones, preparation
    Role: PREP (Preparation)
    (phenyl pyrrolidinylalkyl)

    Bibliographic Information

    1-(3',4'-Methylenedioxyphenyl)-2-pyrrolidinoalkan-1-ones as central
    nervous system stimulants in warm blooded animals. Koeppe,
    Herbert; Ludwig, Gerhard; Zeile, Karl. (Boehringer Ingelheim
    G.m.b.H.). U.S. (1969), 5 pp. CODEN: USXXAM US 3478050
    19691111 Patent written in English. Application: US 66-546197
    19660429. CAN 77:114383 AN 1972:514383 CAPLUS

    Patent Family Information

    Patent No. Kind Date Application No. Date
    US 3478050 A 19691111 US 1966-546197 19660429
    DE 1545591 A 19690807 DE 1965-B82155 19650528

    Priority Application
    DE 1965-B82155 A 19650528

    Abstract

    About 13 1-[3,4-(methylenedioxy)phenyl]-2-(1-pyrrolidinyl)alkanones
    (I, R = H, alkyl; R1 = alkyl) and their hydrochlorides or
    hydrobromides, useful as central nervous system stimulants, were
    prepd. from the bromo ketones (II). I (R = H; R1 = alkyl) were
    prepd. by heating II with pyrrolidine in C6H6-ether at 40-50 or in
    C6H6 at reflux. I (R = alkyl; R1 = alkyl) were prepd. by refluxing
    II with MeONa in MeOH and refluxing the resulting epoxy compds. (III)
    with pyrrolidine. I.HCl and I.HBr were prepd. by acidifying I.

    Patent Classifications

    IPC: C07D; A61K. U.S.: 260326500.

    Indexing -- Section 28-5 (Heterocyclic Compounds (More Than One
    Hetero Atom)

    Supplementary Terms

    benzodioxolyl pyrrolidinyl alkanone; methylenedioxyphenyl
    pyrrolidinyl alkanone; pyrrolidinyl methylenedioxyphenyl alkanone;
    alkanone methylenedioxyphenyl pyrrolidinyl; ketone
    methylenedioxyphenyl pyrrolidinylalkyl; nervous system stimulant
    pyrrolidinylalkanone
    Now the dose info it gives, "0.20, 175 mg/kg, 875" and then benzedrine (racemic amphetamine) 1.95, 80 mg/kg, 42 - now if that first number is supposed to mean a dose for mg/kg, 1.95 seems quite..uh..high for amphetamine? Is it basically saying the dose for MDPV is only about 1/10th the dose of amphetamine? If "theraputic index" for amphetamine is 42, if the LD50 is 80mg/kg / 42 = 1.95, well jesus christ if I weigh 70kg then a theraputic dose of amphetamine is 136mg? Then a dose of MDPV if thats the case is 14mg (so 14mg MDPV sort of "equals" 136mg)?

    Ok, if instead does then 1.4mg MDPV = 13.6mg amphetamine? I don't quite understand (but, if that was the case, that shit is potent!)

    I'll be experimenting with some soon .

    Last edited by yaesutom; 13-07-2005 at 01:29.
     

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    #10
    ^Where did you find this?
     

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    #11
    ^^

    Someone posted it on another forum, *ahem* the forum where a lot of members there seem to love the administrator too much.

    .. nice forum and all i mean, lot of good info there.
     

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    #12
    Bluelighter specialspack's Avatar
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    ^ lol. It's from the CAS system apparently.
     

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    #13
    I thought so too and was hoping that he found a place where it's openly accessible. Oh well, another dream that went down the drain...
     

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    #14
    Bluelighter specialspack's Avatar
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    Sadly no - I assume it was from someone who has access. Is it a subscription based thing?
     

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    #15
    ^unfortunately.
     

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    #16
    Bluelighter Smyth's Avatar
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    yo, be sure to let me how it works out. it looks like some potentially interesting stuff
     

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    #17
    ^^

    It is.. just 5mg gets me going, or 10mg even moreso (and i have a stim tolerance). Its very smooth, no side effects, I guess its like methylphenidate but just really specific and lacks all of ritalin's side effects. Also it lasts much longer, and drops off slow enough to where i'm not even sure when I "come down" it just wears off smoothly.

    I like the stuff, first time I tried it I had already taken some amphetamine earlier so I think the combination is what had me WIRED like I ate 30-40mg dexedrine, but NO jitters, i'd prefer this over methylphenidate based drugs for "ADHD"/focus/alertness/etc anyday .

    Its not really euphoric I guess, - like it couldn't replace cocaine, but it definitely rips methylphenidate a new asshole. I tried snorting some, just 4mg or so, it definitely works this way and kicks in faster - and suprisingly it really didn't burn at all (I was expecting it to the powder has the "look" of a 2C-x). Appetite is good on this stuff.

    I've been taking it for a few days straight now, I find if I do take a little much (10mg then 10mg later on maybe) I definitely get "wired" in the head, body still untouched, but just a tad too focused - there's that "extra dopamine" feeling i can relate in my head to ritalin/coke its just much cleaner.

    I'm buyin' more
     

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    #18
    Bluelighter specialspack's Avatar
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    ^ How does it compare to methamphetamine?

    PS be careful out there yaes, doing a new relatively unknown drug everyday is not the best idea. I don't want to hear about the first MDPV deaths, ok?
     

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    #19
    Well i'd compare it to methylphenidate more than anything, it certainly lacks the euphoria methamphetamine would give you.

    I'm playing around in chemdraw looking at several different stims - cocaine, methylphenidate, MDPV, 1-(p-tolyl)-2-pyrrolidinopentanone, benzylpiperazine, methamphetamine, and if you rotate and/or flip it vertically/horizontally so you can see the similarities between them all, there's obviously noticeable patterns, - just like in the "acid, dragonfly's, and the 5ht2a receptor" thread.

    Interesting.. I think i'll start a new thread on possible new stimulants, some modifications/additions/subtractions in certain ways probably affect potency, selectivity, DA/NE uptake inhibition and release, and euphoria . I'm know the others on this board know way more about how adding this or subtracting that will probably affect it. Interesting shit hehe
     

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    #20
    I have used MDPV three times with doses up to 16mg. The only other stimulants I have used are methylphenidate(ritalin), caffeine, ephedra, modafinil(provigil), and betel nut. All of those are weak except maybe methylphenidate. The only ones I can use what I consider an effective dose of without the side effects getting too bad are modafinil and betel nut. None of them are euphoric.

    MDPV is much better than any of the stimulants I have tried.
    It does not produce much euphoria, just a slight mood lift. For energy or staying awake it is by far the most effective drug I have tried. The duration is pretty long, at least 8 hours. By itself there is nothing recreational about MDPV but when it is combined with opiates it is very enjoyable. I have mixed it with poppies twice and both times were a lot better than the poppies alone. The euphoria is much stronger and I feel more motivated to get things done that I need to do.

    The first time I tried MDPV I used 5mg. The effects were just a little more than threshold. There was a slight increase in energy and alertness. After maybe two hours I took another 3mg. With that the effects became much more noticeable. There was a slight moodlift and I had a lot more energy.

    The second time I ate 16mg(12mg followed by 4mg a few hours later) with poppies and neurontin. It was very pleasant and the MDPV gave me a lot of energy.

    The third time I insufflated 14mg in three doses in combination with poppies and neurontin. My first dose was 14 hours ago and I am still feeling the drugs. This experience has been a lot better than most of my non-psychedelic drug experiences.
    I started with 5mg of MDVP. It hardly burned at all. It kicked in really fast. I was feeling it within a minute or two. During the short come up I felt some euphoria but it only lasted about 5-10 minutes then it quickly faded away. I was left with a slight mood lift and some energy. I was feeling quite lethargic before the MDPV so it helped a lot.
    I took the poppies and neurontin about 15 minutes after the first MDPV dose. When they kicked in they felt a lot better than without MDPV. Two hours later I snorted another 5mg of MDPV. This increased my energy level a lot and also the euphoria. After another 3 or 4 hours I snorted another 4mg.

    I was afraid that MDPV would have some unpleasant side effects because of it's similarities to methylphenidate. Methylphenidate has really bad side effects for me, even at low doses. Fortunately MDPV had little or no side effects. Maybe feeling more tired than I normally would when it wears off. It was late at night both times. I took some today and it is wearing off now, after midnight.

    The second time I used MDPV I checked my blood pressure at wal-mart.
    I checked it 3 times, twice when I first got to the store and again as I was leaving. I had expected that MDPV would raise it some but it did not. The lowest was 126/80 pulse 68 and highest was 135/86 pulse 77. It normally runs between 130/80 pulse 75 and 145/90 pulse 85.
     

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    #21
    ^^ Interesting

    I did notice the slight euphoria when snorting, probably related to the onset time, I just vaporised ~5mg and you could barely tell you were inhaling anything, same slight 'rush' from snorting i guess (not much of one but ya notice it) - instantly wide awake and focused. Hmm, also i've noticed like just now, my hands are extra steady and there's sort of a 'calm' 'dopamine feeling'

    I think also it seems like the best stimulant i've tried for mental alertness/focus but totally lacking any side effects. It would probably be well tolerated if it was prescribed like ritalin/amphetamines, well, better tolerated and less 'abuse potential' (probably less long term damage too but i guess technically we don't really know, but then again most new drugs that come out we really don't know much about the long term effects). Gosh its like I can just barely taste that i've smoked a chemical in my mouth, but, .. kinda tastes good almost.

    Duration is nice, it also seems to wear off so slowly I don't notice a "come down". Its there working and helping you focus and all but you don't feel its 'presence' in the body, heh, yaesutom, shut yo mouth, brotha! you ingested a stimulant and tend to type a little much .
     

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    idea's for new stimulants anyone? 
    #22
    I sat for hours like many times before playing with chemdraw, this is just a bunch of known stimulants (at least most if not all), you can rotate shit around and its kinda like how you can place most psychedelics on top of LSD and it'll line up,



    I don't know much about how to go about designing a stimulant, i drew another page of modified molecules just looking at the patterns from the other ones, probably some percent of the ones i drew would be active, but I really don't know the "rules" with this stuff when it comes to that.

    But lets say, MDPV for example, there a known way or maybe just figuring it out, but if we wanted to make something similar, but maybe less selective (if thats required for euphoria?) and more euphoric, - maybe we'd have to make it less potent then, ahh who knows. I was going to say some more stuff but i'm getting tired and will pass out soon but i'll come back and post whatever it was if i remember .
    Last edited by yaesutom; 17-07-2005 at 20:18.
     

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    #23
    Bluelighter Smyth's Avatar
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    im having trouble transferring the chemsketch file onto the web. it looks shitty when i copy & paste it to paint, and i cant save the chemsketch file as jpg, because it doesn't work (plain & simple).
     

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    #24
    The 4-FA structore is wrong.
     

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    #25
    ^^ yep your right just changed it

    im having trouble transferring the chemsketch file onto the web. it looks shitty when i copy & paste it to paint, and i cant save the chemsketch file as jpg, because it doesn't work (plain & simple).
    Yeah I use chemdraw and lately its been screwing up in wierd ways, i think in that one i posted it drew a white line down the middle, sometimes saving as a gif would just.. come out looking all fucked up for no reason, dunno..
     

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