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Author Topic: fatty acid cannabinoids from mushroom oil like methanandamide  (Read 249 times)

carl_nnabis

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fatty acid cannabinoids from mushroom oil like methanandamide
« on: July 13, 2012, 06:38:41 PM »
so, ive thought about using mushroom oil to make arachidonic acid based cannabinoids like methanandamide, it would be pretty easy, and im still searching if one could obtain mortierella alpinis as living culture, they give nearly 10% at highest in their cellmass, the half cell is filled with arachidonic and hexadecanoic acid!
it would take esterification and then simple ammonolysis with 2-methylethanolamine or on the former acid! I am not sure yet how to make this amine too..
off course, tosylester are of use here as always ;D
no need to say we arent talking about oil spiked with mushrooms for flavour... ;D think this is clear ;D
may of use:
(R)-Methanandamide: A Chiral Novel Anandamide Possessing Higher Potency and Metabolic Stability
J. Med. Chem., 1994, 37 (12), pp 1889–1893
DOI: 10.1021/jm00038a020
« Last Edit: July 13, 2012, 06:42:50 PM by carl_nnabis »
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bubble

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #1 on: July 13, 2012, 06:56:50 PM »
if you don't get your culture you could also use lard as arachidonic acid source which contains 1,7g/100g lard. The seperation is not the easiest but i think it's possible due the different solubilities of the fatty acid salts.

carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #2 on: July 13, 2012, 07:24:58 PM »
but i will culture something else hopefully once haha ;D
i just read about an red algae containing about 1% in its biomass, its name is
Porphyridium cruentum
no reference given sorry just a side note in a german patent, and they mention it can be grown in ponds massively
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JustDreaming

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #3 on: July 22, 2012, 01:13:19 AM »
I always wondered if FAAH inhibitors would increase effects of the fatty acid amide cannabinoids. If you do get around too it it may be worth a shot.
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carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #4 on: July 22, 2012, 01:54:08 AM »
yep, ive read a few papers about them and they do have a direct enhancing effect on the effect!
for example, paracetamol is a easy available FAAH inhibitor, and even thc and related ones will give a maybe feelable example because their effect is also affected trough release of fatty acid hydroxylamides
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carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #5 on: July 22, 2012, 09:18:37 AM »
any tips for a convenient synthesis of isopropanolamin would be appreciated!
 
         CH3
          |
CH3--CH--NH2
          |
         OH

is what i mean in short
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Wizard X

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #6 on: July 23, 2012, 01:20:23 AM »
Quote from: carl_nnabis on July 22, 2012, 09:18:37 AM
any tips for a convenient synthesis of isopropanolamin would be appreciated!
 
         CH3
          |
CH3--C--NH2
          |
         OH

is what i mean in short

CH3-C(-OH)(-NH2)-CH3

Start with acetone, CH3-C(=O)-CH3
« Last Edit: July 23, 2012, 03:36:16 AM by Wizard X »
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lugh

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #7 on: July 23, 2012, 03:10:02 AM »
Quote
any tips for a convenient synthesis of isopropanolamin would be appreciated!

Reduction of acetone oxime results in isopropylamine as the major product  8)
Chemistry is our Covalent Bond

carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #8 on: July 23, 2012, 03:28:39 AM »
yeah but its isopropanOLamine what i need...
anyway i will use ethanolamine and will chlorinate it afterwards amide formation to end up with ACEA, which seems by the way potenter as is methanandamide.
arachidonoylchloroethylamide is its name. maybe a finkelstein swap with potassium bromide will yield a potenter analogue? never heard of arachidonoylbromoethylamide?
i wish i had bought the ACEA when i had the chance to do so a few years ago... but it was so expensive, and was listed as only 80% pure, not the usual 98% rc-standard, so i didnt do so  :(
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carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #9 on: July 23, 2012, 11:32:07 AM »
isopropanolamine would bee possible via isopropylenoxide bromination, then delepine... tasty bromoisopropyloxide...
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Wizard X

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #10 on: July 23, 2012, 11:44:59 AM »
Quote from: carl_nnabis on July 23, 2012, 11:32:07 AM
isopropanolamine would bee possible via isopropylenoxide bromination, then delepine... tasty bromoisopropyloxide...

1-Amino-2-propanol. http://en.wikipedia.org/wiki/1-Amino-2-propanol



Other names...

Isopropanolamine
Monoisopropanolamine
Threamine

1-Amino-2-propanol (Isopropanolamine) is NOT CH3-C(-OH)(-NH2)-CH3 http://127.0.0.1/talk/index.php/topic,3270.msg32641.html#msg32641
« Last Edit: July 23, 2012, 11:50:43 AM by Wizard X »
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bubble

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #11 on: July 23, 2012, 11:49:34 AM »
the work with propylene oxide is also very disgusting because it's toxic and has a really low b.p.. Also it is classed as cancerogen and mutagen. So i think carl would recommend a method without propylene oxide.

carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #12 on: July 24, 2012, 04:19:06 PM »
damned i need arachidonic acid... anyone a good idea how to extract it most convenient?
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carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #13 on: July 24, 2012, 09:13:15 PM »
no worries, i would go the hard way and use thionylchloride ;D
oxalylchlorid is no problem to get too, but its more expensive, nearly doubled price and i dont have any of it yet...and its byproduct are not easily removed, not that problem with SOCl2. also, thionylchloride will chlorinate it equivalent i guess oxalylchloride cannot do this as well.
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carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #14 on: July 25, 2012, 01:21:26 AM »
i guess i have to obtain some mushroom oil containing product, it should be way better suited than lard or something, because it contains only two fatty acids, which can be extracted using hexane, just have to look for a product that contains no shit...
100mg arachidonic acid won from pig liver via phospholidoxidase cost nearly 400 euros at a chem supplier...
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carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #15 on: July 26, 2012, 04:40:45 PM »
I guess a good way to obtain the wanted aminopropanol in enantiomeric purity would be to yeast-reduce the aminoketone maybe. Still looking for a good arachidonic acid product, so that problem has to be solved first.
Even if my opinion is still that the ACEA derivative would be a better choice its more straight forward to synthesize.
Your pdf was very informative regarding the pharmacology. This implies they are indeed a good choice to make!
« Last Edit: July 26, 2012, 04:44:01 PM by carl_nnabis »
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carl_nnabis

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #16 on: July 27, 2012, 01:02:18 AM »
I have made oleamide via transesterification thank you, but this microwaving process looks on paper just hilarious!
I will try it experimentally using ammoniumoleate i think as an experiment to not waste any arachidonic acid...
oleamide is a good sleeping aid, and its pretty good feelable especially as enhancer for other cannabinoids so lets look how this microwave amidation works in reality?
I hope it isnt bogus it just sounds too easily?
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atara

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Re: fatty acid cannabinoids from mushroom oil like methanandamide
« Reply #17 on: July 27, 2012, 08:08:01 AM »
Quote from: carl_nnabis on July 22, 2012, 09:18:37 AM
any tips for a convenient synthesis of isopropanolamin would be appreciated!
 
         CH3
          |
CH3--CH--NH2
          |
         OH

is what i mean in short

The molecule you have drawn is impossible. 1-amino-2-propanol can be obtained by the decarboxylation of threonine, catalyzed by ketones and acids.
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